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</select>
</div>
<div class="include-supplemental-container">
<input type="checkbox" aria-label="Include MeSH and other data" name="include-supplemental" id="email-include-supplemental" class="email-include-supplemental">
<label for="email-include-supplemental" class="email-include-supplemental-label">MeSH and other data</label>
</div>
<div class="form-field recaptcha ">
<div class="g-recaptcha" id="id-recaptcha" data-sitekey="6LfsWHMdAAAAAClKbtOpjQ2pMjgsGxvv7NdZW9uI"></div>
</div>
<div id="captcha-error-message" class="usa-input-error-message captcha-validation-message" role="alert"></div>
<div class="action-panel-actions">
<button class="action-panel-submit"
type="submit"
data-loading-label="Sending..."
data-ga-category="save_share"
data-ga-action="email"
data-ga-label="send">
Send email
</button>
<button class="action-panel-cancel"
aria-label="Close 'Email citations' panel"
ref="linksrc=close_email_panel"
aria-controls="email-action-panel"
aria-expanded="false"
data-ga-category="save_share"
data-ga-action="email"
data-ga-label="cancel">
Cancel
</button>
</div>
<input type="hidden" name="email-search-details" value="" />
<input type="hidden" name="email-search-details-hash" value="0e42663a6c3bd85498fcb88798998fed7bfdc45d457db35281e41afe13cc0524" />
</form>
</div>
</div>
<div id="collections-action-panel"
class="collections-action-panel action-panel in-progress-dots-panel"
aria-hidden="true"
data-collections-open-panel-enabled="false"
data-collections-open-panel-url-hash="#open-collections-panel">
<div class="inner-wrap">
<h3 class="action-panel-heading">
Add to Collections
</h3>
<form id="collections-action-panel-form"
class="collections-action-panel-form action-panel-content action-form action-panel-smaller-selectors"
data-existing-collections-url="/list-existing-collections/"
data-add-to-existing-collection-url="/add-to-existing-collection/"
data-create-and-add-to-new-collection-url="/create-and-add-to-new-collection/"
data-get-article-ids-by-search-url="/get-article-ids-by-search/"
data-myncbi-max-collection-name-length="100"
data-add-to-collection-max-amount="1000"
data-collections-root-url="https://www.ncbi.nlm.nih.gov/myncbi/collections/">
<input type="hidden" name="csrfmiddlewaretoken" value="2SszoR8eoOnyJsvc7bp21Biq8AoTA5x4jFcE1HBAYpa2DTB2Ku24vJO4GE65tG5o">
<div class="choice-group" role="radiogroup">
<ul class="radio-group-items">
<li>
<input type="radio"
id="collections-action-panel-new"
class="collections-new"
name="collections"
value="new"
data-ga-category="save_share"
data-ga-action="collections"
data-ga-label="collections_radio_new">
<label for="collections-action-panel-new">Create a new collection</label>
</li>
<li>
<input type="radio"
id="collections-action-panel-existing"
class="collections-existing"
name="collections"
value="existing"
checked="true"
data-ga-category="save_share"
data-ga-action="collections"
data-ga-label="collections_radio_existing">
<label for="collections-action-panel-existing">Add to an existing collection</label>
</li>
</ul>
</div>
<div class="controls-wrapper">
<div class="action-panel-control-wrap new-collections-controls">
<label for="collections-action-panel-add-to-new" class="action-panel-label required-field-asterisk">
Name your collection:
</label>
<input
type="text"
name="add-to-new-collection"
id="collections-action-panel-add-to-new"
class="collections-action-add-to-new"
pattern="[^&quot;&amp;=&lt;&gt;\/]*" title="The following characters are not allowed in the Name field: &quot;&amp;=&lt;&gt;/"
maxlength="100"
data-ga-category="save_share"
data-ga-action="create_collection"
data-ga-label="non_favorties_collection">
<div class="collections-new-name-too-long usa-input-error-message selection-validation-message">
Name must be less than 100 characters
</div>
</div>
<div class="action-panel-control-wrap existing-collections-controls">
<label for="collections-action-panel-add-to-existing" class="action-panel-label">
Choose a collection:
</label>
<select id="collections-action-panel-add-to-existing"
class="action-panel-selector collections-action-add-to-existing"
data-ga-category="save_share"
data-ga-action="select_collection"
data-ga-label="($('#collections-action-add-to-existing').val() === 'Favorites') ? 'Favorites' : 'non_favorites_collection'">
</select>
<div class="collections-retry-load-on-error usa-input-error-message selection-validation-message">
Unable to load your collection due to an error<br>
<a href="#">Please try again</a>
</div>
</div>
</div>
<div class="action-panel-actions">
<button class="action-panel-submit"
type="submit"
data-loading-label="Adding..."
data-pinger-ignore
data-ga-category="save_share"
data-ga-action="collections"
data-ga-label="add">
Add
</button>
<button class="action-panel-cancel"
aria-label="Close 'Add to Collections' panel"
ref="linksrc=close_collections_panel"
aria-controls="collections-action-panel"
aria-expanded="false"
data-ga-category="save_share"
data-ga-action="collections"
data-ga-label="cancel">
Cancel
</button>
</div>
</form>
</div>
</div>
<div id="bibliography-action-panel"
class="bibliography-action-panel action-panel in-progress-dots-panel"
aria-hidden="true"
data-bibliography-open-panel-enabled="false"
data-bibliography-open-panel-url-hash="#open-bibliography-panel">
<div class="inner-wrap">
<h3 class="action-panel-heading">
Add to My Bibliography
</h3>
<form id="bibliography-action-panel-form"
class="bibliography-action-panel-form action-panel-content action-form action-panel-smaller-selectors"
data-add-to-bibliography-max-amount="100"
data-add-to-bibliography-batch-size="10"
data-bibliography-delegates-url="/list-bibliography-delegates/"
data-add-to-bibliography-url="/add-to-bibliography/"
data-get-article-ids-by-search-url="/get-article-ids-by-search/"
data-mybib-root-url="https://www.ncbi.nlm.nih.gov/myncbi/collections/mybibliography/">
<input type="hidden" name="csrfmiddlewaretoken" value="2SszoR8eoOnyJsvc7bp21Biq8AoTA5x4jFcE1HBAYpa2DTB2Ku24vJO4GE65tG5o">
<div class="action-panel-control-wrap bibliographies-controls">
<div class="choice-group">
<ul class="bibliographies-action-add radio-group-items">
<li>
<input name="bibliography" id="my-bibliography" class="my-bibliography" type="radio" checked/>
<label for="my-bibliography">My Bibliography</label>
</li>
</ul>
</div>
</div>
<div class="bibliographies-retry-load-on-error usa-input-error-message selection-validation-message">
Unable to load your delegates due to an error<br>
<a href="#">Please try again</a>
</div>
<div class="action-panel-actions">
<button class="action-panel-submit"
type="submit"
data-loading-label="Adding..."
data-pinger-ignore>
Add
</button>
<button class="action-panel-cancel"
aria-label="Close 'Add to bibliography' panel"
ref="linksrc=close_bibliography_panel"
aria-controls="bibliography-action-panel"
aria-expanded="false"
data-ga-category="save_share"
data-ga-action="mybib"
data-ga-label="cancel">
Cancel
</button>
</div>
</form>
</div>
</div>
<div id="saved-search-action-panel" class="saved-search-action-panel action-panel " aria-hidden="true"
data-saved-search-open-panel-enabled="false"
data-saved-search-open-panel-url-hash="#open-saved-search-panel">
<div class="inner-wrap">
<h2 class="action-panel-heading">
Your saved search
</h2>
<form id="saved-search-action-panel-form"
class="saved-search-action-panel-form action-panel-content action-form"
data-create-saved-search-url="/create-saved-search/"
data-try-search-terms-url="/try-search-term/"
data-saved-search-root-url="https://www.ncbi.nlm.nih.gov/myncbi/searches/">
<input type="hidden" name="csrfmiddlewaretoken" value="2SszoR8eoOnyJsvc7bp21Biq8AoTA5x4jFcE1HBAYpa2DTB2Ku24vJO4GE65tG5o">
<div class="action-panel-control-wrap">
<label for="saved-search-name" class="action-panel-label saved-search-name-label required-field-asterisk">
Name of saved search:
</label>
<input maxlength="200"
type="text"
name="saved-search-name"
id="saved-search-name"
class="saved-search-name"
value=""
required
pattern="[^&quot;&amp;=&lt;&gt;\/]*" title="The following characters are not allowed in the Name field: &quot;&amp;=&lt;&gt;/">
</div>
<div class="action-panel-control-wrap">
<label for="saved-search-term" class="action-panel-label required-field-asterisk">
Search terms:
</label>
<textarea name="saved-search-term" id="saved-search-term" class="saved-search-term" required></textarea>
</div>
<div class="test-search-term-wrap">
<a href="#" class="try-search-term">Test search terms</a>
</div>
<div class="choice-group action-panel-extra-margin-top">
<span class="action-panel-label" id="fieldset-label">
Would you like email updates of new search results?
</span>
<fieldset id="saved-search-alert" aria-describedby="fieldset-label">
<legend class="usa-sr-only">Saved Search Alert Radio Buttons</legend>
<ul class="radio-group-items">
<li>
<input type="radio" id="saved-search-alert-yes" class="saved-search-alert-yes" name="saved-search-alert" value="yes" checked>
<label for="saved-search-alert-yes" class="action-panel-label">Yes</label>
</li>
<li>
<input aria-label="No radio input" type="radio" id="saved-search-alert-no" class="saved-search-alert-no" name="saved-search-alert" value="no">
<label for="saved-search-alert-no" class="action-panel-label">No</label>
</li>
</ul>
</fieldset>
</div>
<div class="alert-schedule-wrap">
<div class="action-panel-control-wrap">
<label class="action-panel-label">
Email:
</label>
<span aria-label="Email address" id="saved-search-email" class="action-panel-label"><span class="action-panel-label-bold"></span> (<a class="myncbi-account-settings" href="https://www.ncbi.nlm.nih.gov/account/settings/">change</a>)</span>
</div>
<div class="action-panel-control-wrap action-panel-extra-margin-top">
<label for="saved-search-frequency" class="action-panel-label">
Frequency:
</label>
<select id="saved-search-frequency" class="no-border-panel-selector saved-search-frequency">
<option value="monthly">Monthly</option>
<option value="weekly">Weekly</option>
<option value="daily">Daily</option>
</select>
</div>
<div class="action-panel-control-wrap saved-search-monthly-additional">
<label for="saved-search-monthly-on-day" class="action-panel-label">
Which day?
</label>
<select id="saved-search-monthly-on-day" class="no-border-panel-selector">
<option value="Sunday">The first Sunday</option>
<option value="Monday">The first Monday</option>
<option value="Tuesday">The first Tuesday</option>
<option value="Wednesday">The first Wednesday</option>
<option value="Thursday">The first Thursday</option>
<option value="Friday">The first Friday</option>
<option value="Saturday">The first Saturday</option>
<option value="day">The first day</option>
<option value="weekday">The first weekday</option>
</select>
</div>
<div class="action-panel-control-wrap saved-search-weekly-additional">
<label for="saved-search-weekly-on-day" class="action-panel-label">
Which day?
</label>
<select id="saved-search-weekly-on-day" class="no-border-panel-selector saved-search-weekly-on-day">
<option value="Sunday">Sunday</option>
<option value="Monday">Monday</option>
<option value="Tuesday">Tuesday</option>
<option value="Wednesday">Wednesday</option>
<option value="Thursday">Thursday</option>
<option value="Friday">Friday</option>
<option value="Saturday">Saturday</option>
</select>
</div>
<div class="action-panel-control-wrap">
<label for="saved-search-report" class="action-panel-label">
Report format:
</label>
<select id="saved-search-report" class="no-border-panel-selector saved-search-report">
<option value="DocSum">Summary</option>
<option value="DocSumText">Summary (text)</option>
<option value="Abstract">Abstract</option>
<option value="AbstractText">Abstract (text)</option>
<option value="MEDLINE">PubMed</option>
</select>
</div>
<div class="action-panel-control-wrap">
<label for="saved-search-amount" class="action-panel-label">
Send at most:
</label>
<select id="saved-search-amount" class="no-border-panel-selector saved-search-amount">
<option value="1">1 item</option>
<option value="5" selected>5 items</option>
<option value="10">10 items</option>
<option value="20">20 items</option>
<option value="50">50 items</option>
<option value="100">100 items</option>
<option value="200">200 items</option>
</select>
</div>
<div>
<input type="checkbox" id="saved-search-send-if-no-result" class="saved-search-send-if-no-result" name="saved-search-send-if-no-result">
<label for="saved-search-send-if-no-result" class="action-panel-label smaller-checkbox">
Send even when there aren't any new results
</label>
</div>
<div class="action-panel-control-wrap option-text-in-email-wrap">
<label for="saved-search-email-text" class="action-panel-label">
Optional text in email:
</label>
<textarea name="saved-search-email-text"
id="saved-search-email-text"
class="saved-search-email-text"></textarea>
</div>
</div>
<div class="action-panel-actions">
<button class="action-panel-submit"
type="submit"
data-loading-label="Saving..."
data-ga-category="save_share"
data-ga-action="alert"
data-ga-label="save">
Save
</button>
<button class="action-panel-cancel"
aria-label="Close 'Your saved search' panel"
ref="linksrc=close_saved_search_panel"
aria-controls="saved-search-action-panel"
aria-expanded="false"
data-ga-category="save_share"
data-ga-action="alert"
data-ga-label="cancel">
Cancel
</button>
</div>
</form>
</div>
</div>
<div id="citation-manager-action-panel" class="citation-manager-action-panel action-panel" aria-hidden="true">
<div class="inner-wrap">
<h2 class="action-panel-heading">
Create a file for external citation management software
</h2>
<form id="citation-manager-action-panel-form"
class="action-panel-content action-form"
action="/results-export-ids/"
data-by-search-action="/results-export-search-data/"
data-by-ids-action="/results-export-ids/"
method="post"
data-by-search-method="post"
data-by-ids-method="post">
<input type="hidden" name="csrfmiddlewaretoken" value="2SszoR8eoOnyJsvc7bp21Biq8AoTA5x4jFcE1HBAYpa2DTB2Ku24vJO4GE65tG5o">
<input name="results-format" type="hidden" value="pubmed"/>
<div class="action-panel-actions">
<button class="action-panel-submit"
type="submit"
data-loading-label="Sending..."
data-ga-category="save_share"
data-ga-action="citation_manager"
data-ga-label="save">
Create file
</button>
<button class="action-panel-cancel"
aria-label="Close 'Send citations to citation manager' panel"
ref="linksrc=close_citation_manager_panel"
aria-controls="citation-manager-action-panel"
aria-expanded="false"
data-ga-category="save_share"
data-ga-action="citation_manager"
data-ga-label="cancel">
Cancel
</button>
</div>
</form>
</div>
</div>
<div id="rss-action-panel" class="rss-action-panel action-panel " aria-hidden="true">
<div class="inner-wrap">
<h2 class="action-panel-heading">
Your RSS Feed
</h2>
<form id="rss-action-panel-form"
class="rss-action-panel-form action-panel-content action-form"
data-create-rss-feed-url="/create-rss-feed-url/"
data-search-form-term-value="">
<input type="hidden" name="csrfmiddlewaretoken" value="2SszoR8eoOnyJsvc7bp21Biq8AoTA5x4jFcE1HBAYpa2DTB2Ku24vJO4GE65tG5o">
<div class="action-panel-control-wrap">
<label for="rss-name" class="action-panel-label required-field-asterisk">
Name of RSS Feed:
</label>
<input maxlength="200"
placeholder="Name"
type="text"
name="rss-name"
id="rss-name"
class="rss-name"
value=''
required
pattern="[^&quot;&amp;=&lt;&gt;\/]*" title="The following characters are not allowed in the Name field: &quot;&amp;=&lt;&gt;/">
</div>
<div class="rss-limit-wrap">
<div class="action-panel-control-wrap action-panel-extra-margin-top">
<label for="rss-limit" class="action-panel-label">
Number of items displayed:
</label>
<select id="rss-limit" class="no-border-panel-selector rss-limit">
<option value="5">5</option>
<option value="10">10</option>
<option value="15" selected="selected">15</option>
<option value="20">20</option>
<option value="50">50</option>
<option value="100">100</option>
</select>
</div>
</div>
<div class="action-panel-actions">
<button class="action-panel-submit"
type="submit"
data-loading-label="Creating..."
data-ga-category="save_share"
data-ga-action="alert"
data-ga-label="save">
Create RSS
</button>
<button class="action-panel-cancel"
aria-label="Close 'Your RSS' panel"
ref="linksrc=close_rss_panel"
aria-controls="rss-action-panel"
aria-expanded="false"
data-ga-category="save_share"
data-ga-action="alert"
data-ga-label="cancel">
Cancel
</button>
</div>
<div class="action-panel-control-wrap rss-link-copy-wrap">
<label for="rss-link" class="usa-sr-only">RSS Link</label>
<input placeholder="Your RSS Feed Link" type="text" name="rss-link" id="rss-link" class="rss-link" title="RSS Link">
<button
type="button"
disabled
class="rss-link-copy-button disabled"
data-ga-category="save_share"
data-ga-action="rss"
data-ga-label="copy">
Copy
</button>
</div>
</form>
</div>
</div>
</div>
</div>
<div class="article-page" id="article-page" data-article-pmid="27294709">
<aside class="page-sidebar">
<div class="inner-wrap">
<div class="full-text-links">
<div class="full-view">
<h3 class="title">
Full text links
</h3>
<div class="full-text-links-list">
<a class="link-item
dialog-focus"
href="https://doi.org/10.1021/acs.accounts.6b00164"
target="_blank"
rel="noopener"
ref="linksrc=fulltextorjournal_fulltext&amp;is_pmc=False&amp;PrId=3001&amp;itool=Abstract-def&amp;log$=linkouticon&amp;uid=27294709&amp;db=pubmed&amp;nlmid=0157313"
title="See full text options at American Chemical Society"
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data-ga-action="American Chemical Society"
data-ga-label="27294709"
><img src="https://cdn.ncbi.nlm.nih.gov/corehtml/query/egifs/http:--pubs.acs.org-images-pubmed-acspubs.jpg" alt="American Chemical Society full text link"><span class="text">
American Chemical Society
</span></a><a class="link-item
pmc
"
href="https://pmc.ncbi.nlm.nih.gov/articles/pmid/27294709/"
target="_blank"
rel="noopener"
ref="linksrc=fulltextorjournal_fulltext&amp;is_pmc=True&amp;PrId=3494&amp;itool=Abstract-def&amp;log$=linkouticon&amp;uid=27294709&amp;db=pubmed&amp;nlmid=0157313"
title="Free full text at PubMed Central"
data-ga-category="full_text"
data-ga-action="PMC"
data-ga-label="27294709"
><span class="text">
Free PMC article
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<div class="short-view">
<a href="#" class="full-text-links-button full-text-links-dialog-trigger">
Full text links
</a>
</div>
</div>
<div class="actions-buttons sidebar"><h3 class="title">Actions</h3><div class="inner-wrap"><button class="citation-button citation-dialog-trigger"
aria-label="Open dialog with citation text in different styles"
data-ga-category="save_share"
data-ga-action="cite"
data-ga-label="open"
data-all-citations-url="/27294709/citations/"
data-citation-style="nlm"
data-pubmed-format-link="/27294709/export/"><span class="button-label">Cite</span></button><link type="text/css" href="ncbi-overlay-block/src/overlay-block.css"><div class="collections-button-container" data-article-id="27294709" data-article-db="pubmed"><button class="collections-button collections-dialog-trigger"
aria-label="Save article in MyNCBI collections."
data-ga-category="collections_button"
data-ga-action="click"
data-ga-label="collections_button"
data-collections-open-dialog-enabled="false"
data-collections-open-dialog-url="https://account.ncbi.nlm.nih.gov/?back_url=https%3A%2F%2Fpubmed.ncbi.nlm.nih.gov%2F27294709%2F%23open-collections-dialog"
data-in-collections="false"><span class="button-label">Collections</span></button><div class="overlay" role="dialog"><div id="collections-action-dialog"
class="dialog collections-dialog"
aria-hidden="true"><div class="title">Add to Collections</div><div class="collections-action-panel action-panel"><form id="collections-action-dialog-form"
class="collections-action-panel-form action-panel-content action-form action-panel-smaller-selectors"
data-existing-collections-url="/list-existing-collections/"
data-add-to-existing-collection-url="/add-to-existing-collection/"
data-create-and-add-to-new-collection-url="/create-and-add-to-new-collection/"
data-myncbi-max-collection-name-length="100"
data-collections-root-url="https://www.ncbi.nlm.nih.gov/myncbi/collections/"><input type="hidden" name="csrfmiddlewaretoken" value="2SszoR8eoOnyJsvc7bp21Biq8AoTA5x4jFcE1HBAYpa2DTB2Ku24vJO4GE65tG5o"><div class="choice-group" role="radiogroup"><ul class="radio-group-items"><li><input type="radio"
id="collections-action-dialog-new"
class="collections-new"
name="collections"
value="new"
data-ga-category="collections_button"
data-ga-action="click"
data-ga-label="collections_radio_new"><label for="collections-action-dialog-new">Create a new collection</label></li><li><input type="radio"
id="collections-action-dialog-existing"
class="collections-existing"
name="collections"
value="existing"
checked="true"
data-ga-category="collections_button"
data-ga-action="click"
data-ga-label="collections_radio_existing"><label for="collections-action-dialog-existing">Add to an existing collection</label></li></ul></div><div class="controls-wrapper"><div class="action-panel-control-wrap new-collections-controls"><label for="collections-action-dialog-add-to-new" class="action-panel-label required-field-asterisk">
Name your collection:
</label><input
type="text"
name="add-to-new-collection"
id="collections-action-dialog-add-to-new"
class="collections-action-add-to-new"
pattern="[^&quot;&amp;=&lt;&gt;\/]*" title="The following characters are not allowed in the Name field: &quot;&amp;=&lt;&gt;/"
maxlength="100"
data-ga-category="collections_button"
data-ga-action="create_collection"
data-ga-label="non_favorties_collection"><div class="collections-new-name-too-long usa-input-error-message selection-validation-message">
Name must be less than 100 characters
</div></div><div class="action-panel-control-wrap existing-collections-controls"><label for="collections-action-dialog-add-to-existing" class="action-panel-label">
Choose a collection:
</label><select id="collections-action-dialog-add-to-existing"
class="action-panel-selector collections-action-add-to-existing"
data-ga-category="collections_button"
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The cell surface (or cell wall) of bacteria is coated with carbohydrate (or glycan) structures that play a number of important roles. These include providing structural integrity, serving as a permeability barrier to extracellular compounds (e.g., drugs) and modulating the immune system of the host. Of interest to this Account is the cell wall structure of mycobacteria. There are a host of different mycobacterial species, some of which cause human disease. The most well-known is Mycobacterium tuberculosis, the causative agent of tuberculosis. The mycobacterial cell wall is characterized by the presence of unusual carbohydrate structures that fulfill the roles described above. However, in many cases, a molecular-level understanding of how mycobacterial cell wall glycans mediate these processes is lacking. Inspired by a seminar he heard as a postdoctoral fellow, the author began his independent research program with a focus on the chemical synthesis of mycobacterial glycans. The goals were not only to develop synthetic approaches to these unique structures but also to provide molecules that could be used to probe their biological function. Initial work addressed the preparation of fragments of two key polysaccharides, arabinogalactan and lipoarabinomannan, which contain large numbers of sugar residues in the furanose (five-membered) ring form. At the time these investigations began, there were few methods reported for the synthesis of oligosaccharides containing furanose rings. Thus, early in the program, a major area of interest was methodology development, particularly for the preparation of 1,2-cis-furanosides. To solve this challenge, a range of conformationally restricted donors have been developed, both in the author's group and others, which provide 1,2-cis-furanosidic linkages with high stereoselectivity. These investigations were followed by application of the developed methods to the synthesis of a range of target molecules containing arabinofuranose and galactofuranose residues. These molecules have now found application in biochemical, immunological, and structural biology investigations, which have shed light on their biosynthesis and how these motifs are recognized by both the innate and adaptive immune systems. More recently, attention has been directed toward the synthesis of another class of immunologically active mycobacterial cell wall glycans, the extractable glycolipids. In this case, efforts have been primarily on phenolic glycolipids, and the compounds synthesized have been used to evaluate their ability to modulate cytokine release. Over the past 20 years, the use of chemical synthesis to provide increasingly complex glycan structures has provided significant benefit to the burgeoning field of mycobacterial glycobiology. Through the efforts of groups from around the globe, access to these compounds is now possible via relatively straightforward methods. As the pool of mycobacterial glycans continues to grow, so too will our understanding of their role in disease, which will undoubtedly lead to new strategies to prevent or treat mycobacterial infections.
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<div class="figure-caption-contents"><p> Representation of the mycobacterial cell… </p></div>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Figure 1 </p>
</strong>
<div class="figure-caption-contents"><p> Representation of the mycobacterial cell wall with all major classes of glycans shown.… </p></div>
</div>
<figcaption id="figure-caption-0" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Figure 1
</strong>
<div class="figure-caption-contents">Representation of the mycobacterial cell wall with all
major classes
of glycans shown. LAM, lipoarabinomannan; PGLs, phenolic glycolipids;
GPLs, glycopeptidolipids; LOSs, lipooligosaccharides. Reproduced with
permission from ref (5). Copyright 2015 John Wiley & Sons.</div>
</figcaption>
</figure>
<figure class="figure-item "
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="1"
data-label-slug="figure-2">
<a class="figure-link"
href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/e99ab9d356d0/ar-2016-001647_0002.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-1"
role="button"
data-image-width="789"
data-image-height="971"
data-image-alt="Figure 2"
data-pmc-id="PMC4955529"
data-figure-id="fig2">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-1"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/1dd0cf99efd3/ar-2016-001647_0002.gif"
alt="Figure 2" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="789">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="971">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Figure 2 </p>
</strong>
<div class="figure-caption-contents"><p> Composite structures of mycobacterial arabinogalactan… </p></div>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Figure 2 </p>
</strong>
<div class="figure-caption-contents"><p> Composite structures of mycobacterial arabinogalactan (AG) and lipoarabinomannan (LAM). </p></div>
</div>
<figcaption id="figure-caption-1" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Figure 2
</strong>
<div class="figure-caption-contents">Composite structures of mycobacterial arabinogalactan (AG) and
lipoarabinomannan (LAM).</div>
</figcaption>
</figure>
<figure class="figure-item "
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="2"
data-label-slug="scheme-1">
<a class="figure-link"
href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/ae575caf80bf/ar-2016-001647_0011.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-2"
role="button"
data-image-width="765"
data-image-height="270"
data-image-alt="Scheme 1"
data-pmc-id="PMC4955529"
data-figure-id="sch1">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-2"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/3abdf378e01f/ar-2016-001647_0011.gif"
alt="Scheme 1" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="765">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="270">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Scheme 1. Access to the Arabinofuranose Ring… </p>
</strong>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Scheme 1. Access to the Arabinofuranose Ring System and Donors ( <b> 3 </b> <b> 5 </b> )… </p>
</strong>
</div>
<figcaption id="figure-caption-2" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Scheme 1. Access to the Arabinofuranose Ring System and Donors (<b>3</b><b>5</b>) for the Synthesis of Arabinofuranose-Containing Glycans
</strong>
</figcaption>
</figure>
<figure class="figure-item "
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="3"
data-label-slug="figure-3">
<a class="figure-link"
href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/3616cac37bd8/ar-2016-001647_0003.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-3"
role="button"
data-image-width="723"
data-image-height="552"
data-image-alt="Figure 3"
data-pmc-id="PMC4955529"
data-figure-id="fig3">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-3"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/68ff683c78af/ar-2016-001647_0003.gif"
alt="Figure 3" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="723">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="552">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Figure 3 </p>
</strong>
<div class="figure-caption-contents"><p> (A) Structures of the α-Ara… </p></div>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Figure 3 </p>
</strong>
<div class="figure-caption-contents"><p> (A) Structures of the α-Ara <i> f </i> and β-Ara <i> f </i> ring systems and (B)… </p></div>
</div>
<figcaption id="figure-caption-3" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Figure 3
</strong>
<div class="figure-caption-contents">(A) Structures of the α-Ara<i>f</i> and
β-Ara<i>f</i> ring systems and (B) structures of α-Ara<i>f</i>-containing oligosaccharides <b>8</b> and <b>9</b>.</div>
</figcaption>
</figure>
<figure class="figure-item "
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="4"
data-label-slug="figure-4">
<a class="figure-link"
href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/6365f614a8cd/ar-2016-001647_0004.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-4"
role="button"
data-image-width="675"
data-image-height="839"
data-image-alt="Figure 4"
data-pmc-id="PMC4955529"
data-figure-id="fig4">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-4"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/bfff9407f7a1/ar-2016-001647_0004.gif"
alt="Figure 4" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="675">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="839">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Figure 4 </p>
</strong>
<div class="figure-caption-contents"><p> Structure of the Ara6 motif… </p></div>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Figure 4 </p>
</strong>
<div class="figure-caption-contents"><p> Structure of the Ara6 motif (as the methyl glycoside), which is present in… </p></div>
</div>
<figcaption id="figure-caption-4" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Figure 4
</strong>
<div class="figure-caption-contents">Structure of the Ara6 motif (as the methyl
glycoside), which is
present in both AG and LAM.</div>
</figcaption>
</figure>
<figure class="figure-item "
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="5"
data-label-slug="figure-5">
<a class="figure-link"
href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/c2a46bc9a3a4/ar-2016-001647_0005.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-5"
role="button"
data-image-width="788"
data-image-height="401"
data-image-alt="Figure 5"
data-pmc-id="PMC4955529"
data-figure-id="fig5">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-5"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/e6757c496ed1/ar-2016-001647_0005.gif"
alt="Figure 5" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="788">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="401">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Figure 5 </p>
</strong>
<div class="figure-caption-contents"><p> (A) Studies by Crich on… </p></div>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Figure 5 </p>
</strong>
<div class="figure-caption-contents"><p> (A) Studies by Crich on the synthesis of β-mannopyranosides, showing the β-selective glycosyl… </p></div>
</div>
<figcaption id="figure-caption-5" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Figure 5
</strong>
<div class="figure-caption-contents">(A)
Studies by Crich on the synthesis of β-mannopyranosides,
showing the β-selective glycosyl triflate intermediate (<b>15</b>) and an α-selective/unselective intermediate (<b>16</b>). (B) A conformationally restricted
Ara<i>f</i>-thioglycoside (<b>17</b>).</div>
</figcaption>
</figure>
<figure class="figure-item tail"
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="6"
data-label-slug="figure-6">
<a class="figure-link"
href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/73ac5aa92b18/ar-2016-001647_0006.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-6"
role="button"
data-image-width="757"
data-image-height="147"
data-image-alt="Figure 6"
data-pmc-id="PMC4955529"
data-figure-id="fig6">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-6"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/3bcf191f59e2/ar-2016-001647_0006.gif"
alt="Figure 6" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="757">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="147">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Figure 6 </p>
</strong>
<div class="figure-caption-contents"><p> (A) 2,3-anhydrosugar donors <b> 18a/18b </b> and… </p></div>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Figure 6 </p>
</strong>
<div class="figure-caption-contents"><p> (A) 2,3-anhydrosugar donors <b> 18a/18b </b> and their use in the synthesis of β-arabinofuranosides (… </p></div>
</div>
<figcaption id="figure-caption-6" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Figure 6
</strong>
<div class="figure-caption-contents">(A) 2,3-anhydrosugar
donors <b>18a/18b</b> and their use
in the synthesis of β-arabinofuranosides (<b>20</b>).
(B) Postulated complex (<b>21</b>) formed in ()-sparteine-mediated
nucleophilic opening of O-5 deprotonated 2,3-anhydro-β-<sc>d</sc>-lyxofuranosides (e.g., <b>19</b>) by lithium alkoxides.</div>
</figcaption>
</figure>
<figure class="figure-item tail"
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="7"
data-label-slug="figure-7">
<a class="figure-link"
href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/e9e53d72786d/ar-2016-001647_0007.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-7"
role="button"
data-image-width="791"
data-image-height="120"
data-image-alt="Figure 7"
data-pmc-id="PMC4955529"
data-figure-id="fig7">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-7"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/70018836be19/ar-2016-001647_0007.gif"
alt="Figure 7" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="791">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="120">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Figure 7 </p>
</strong>
<div class="figure-caption-contents"><p> Conformationally restricted arabinofuranose donors (… </p></div>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Figure 7 </p>
</strong>
<div class="figure-caption-contents"><p> Conformationally restricted arabinofuranose donors ( <b> 22 </b> <b> 25 </b> , <b> 27 </b> ) and an… </p></div>
</div>
<figcaption id="figure-caption-7" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Figure 7
</strong>
<div class="figure-caption-contents">Conformationally
restricted arabinofuranose donors (<b>22</b><b>25</b>, <b>27</b>) and an O-5 substituted
β-arabinofuranoside motif present in mycobacterial LAM (<b>26</b>).</div>
</figcaption>
</figure>
<figure class="figure-item tail"
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="8"
data-label-slug="scheme-2">
<a class="figure-link"
href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/96a5538a59e7/ar-2016-001647_0012.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-8"
role="button"
data-image-width="753"
data-image-height="142"
data-image-alt="Scheme 2"
data-pmc-id="PMC4955529"
data-figure-id="sch2">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-8"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/a6af89b51c4b/ar-2016-001647_0012.gif"
alt="Scheme 2" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="753">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="142">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Scheme 2. Access to the Galactofuranose Ring… </p>
</strong>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Scheme 2. Access to the Galactofuranose Ring System from Dithioacetal <b> 28 </b> and Donors ( <b> 31… </b> </p>
</strong>
</div>
<figcaption id="figure-caption-8" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Scheme 2. Access to the Galactofuranose Ring System from Dithioacetal <b>28</b> and Donors (<b>31</b> and <b>32</b>) Used in the Synthesis of β-Galactofuranosides
</strong>
</figcaption>
</figure>
<figure class="figure-item tail"
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="9"
data-label-slug="figure-8">
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href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/6d0824548750/ar-2016-001647_0008.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-9"
role="button"
data-image-width="778"
data-image-height="685"
data-image-alt="Figure 8"
data-pmc-id="PMC4955529"
data-figure-id="fig8">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-9"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/f10935577aa3/ar-2016-001647_0008.gif"
alt="Figure 8" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="778">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="685">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Figure 8 </p>
</strong>
<div class="figure-caption-contents"><p> Representative structures of synthetic β-galactofuranoside… </p></div>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Figure 8 </p>
</strong>
<div class="figure-caption-contents"><p> Representative structures of synthetic β-galactofuranoside fragments of mycobacterial AG. </p></div>
</div>
<figcaption id="figure-caption-9" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Figure 8
</strong>
<div class="figure-caption-contents">Representative structures of synthetic β-galactofuranoside
fragments of mycobacterial AG.</div>
</figcaption>
</figure>
<figure class="figure-item tail"
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="10"
data-label-slug="figure-9">
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href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/0cfd4cfd2189/ar-2016-001647_0009.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-10"
role="button"
data-image-width="789"
data-image-height="443"
data-image-alt="Figure 9"
data-pmc-id="PMC4955529"
data-figure-id="fig9">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-10"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/4dfa888d83da/ar-2016-001647_0009.gif"
alt="Figure 9" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="789">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="443">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Figure 9 </p>
</strong>
<div class="figure-caption-contents"><p> Representative structures of phenolic glycolipids… </p></div>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Figure 9 </p>
</strong>
<div class="figure-caption-contents"><p> Representative structures of phenolic glycolipids ( <b> 34 </b> ), glycopeptidolipids ( <b> 35 </b> ), trehalose… </p></div>
</div>
<figcaption id="figure-caption-10" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Figure 9
</strong>
<div class="figure-caption-contents">Representative structures
of phenolic glycolipids (<b>34</b>), glycopeptidolipids (<b>35</b>), trehalose mycolates (<b>36</b>), and lipooligosaccharides
(<b>37</b>).</div>
</figcaption>
</figure>
<figure class="figure-item tail"
itemscope itemtype="http://schema.org/ImageObject"
itemprop="associatedMedia"
data-slide-index="11"
data-label-slug="figure-10">
<a class="figure-link"
href="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/db1bedbd454c/ar-2016-001647_0010.jpg"
itemprop="contentUrl"
aria-describedby="figure-caption-11"
role="button"
data-image-width="776"
data-image-height="1246"
data-image-alt="Figure 10"
data-pmc-id="PMC4955529"
data-figure-id="fig10">
<img class="figure-thumb" itemprop="thumbnail"
id="article-image-11"
src="https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4a2e/4955529/5e235751fe50/ar-2016-001647_0010.gif"
alt="Figure 10" />
</a>
<meta itemprop="width" itemtype="http://schema.org/ImageObject" content="776">
<meta itemprop="height" itemtype="http://schema.org/ImageObject" content="1246">
<div class="figure-caption figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="caption" aria-hidden="true">
<div class="caption-wrap">
<strong class="figure-label">
<p> Figure 10 </p>
</strong>
<div class="figure-caption-contents"><p> Synthetic PGL analogs used to… </p></div>
</div>
</div>
<div class="figure-caption-medium figure-caption-text" aria-hidden="true">
<strong class="figure-label">
<p> Figure 10 </p>
</strong>
<div class="figure-caption-contents"><p> Synthetic PGL analogs used to probe cytokine modulation. </p></div>
</div>
<figcaption id="figure-caption-11" class="figure-caption-full figure-caption-text" itemtype="http://schema.org/ImageObject" itemprop="description">
<strong class="figure-label">
Figure 10
</strong>
<div class="figure-caption-contents">Synthetic PGL analogs used to probe cytokine
modulation.</div>
</figcaption>
</figure>
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