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<meta name="robots" content="INDEX,FOLLOW,NOARCHIVE" /><meta name="citation_inbook_title" content="Glycoscience Protocols (GlycoPODv2) [Internet]" /><meta name="citation_title" content="Conversion of pyridylamino sugar chains to corresponding reducing sugar chains" /><meta name="citation_publisher" content="Japan Consortium for Glycobiology and Glycotechnology" /><meta name="citation_date" content="2022/03/21" /><meta name="citation_author" content="Shin-ichi Nakakita" /><meta name="citation_pmid" content="37590670" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK593933/" /><meta name="citation_keywords" content="pyridylamino" /><meta name="citation_keywords" content="1-amino-1-deoxy derivative" /><meta name="citation_keywords" content="conversion" /><meta name="citation_keywords" content="reducing sugar" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="Conversion of pyridylamino sugar chains to corresponding reducing sugar chains" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="Japan Consortium for Glycobiology and Glycotechnology" /><meta name="DC.Contributor" content="Shin-ichi Nakakita" /><meta name="DC.Date" content="2022/03/21" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK593933/" /><meta name="description" content="Pyridylamino (PA) saccharides can be converted into the corresponding reducing sugar chains using a two-step process (Figure 1). The first step is its conversion into 1-amino-l-deoxy derivatives, and the second is its conversion into the corresponding reducing sugar chains using the Sommelet reaction (1, 2)." /><meta name="og:title" content="Conversion of pyridylamino sugar chains to corresponding reducing sugar chains" /><meta name="og:type" content="book" /><meta name="og:description" content="Pyridylamino (PA) saccharides can be converted into the corresponding reducing sugar chains using a two-step process (Figure 1). The first step is its conversion into 1-amino-l-deoxy derivatives, and the second is its conversion into the corresponding reducing sugar chains using the Sommelet reaction (1, 2)." /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK593933/" /><meta name="og:site_name" content="NCBI Bookshelf" /><meta name="og:image" content="https://www.ncbi.nlm.nih.gov/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-glycopodv2-lrg.png" /><meta name="twitter:card" content="summary" /><meta name="twitter:site" content="@ncbibooks" /><meta name="bk-non-canon-loc" content="/books/n/glycopodv2/g128-pyridylamino/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK593933/" /><link rel="stylesheet" href="/corehtml/pmc/css/figpopup.css" type="text/css" media="screen" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books.min.css" type="text/css" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books_print.min.css" type="text/css" /><style type="text/css">p a.figpopup{display:inline !important} .bk_tt {font-family: monospace} .first-line-outdent .bk_ref {display: inline} </style><script type="text/javascript" src="/corehtml/pmc/js/jquery.hoverIntent.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/common.min.js?_=3.18"> </script><script type="text/javascript">window.name="mainwindow";</script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/book-toc.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/books.min.js"> </script>
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<div class="pre-content"><div><div class="bk_prnt"><p class="small">NCBI Bookshelf. A service of the National Library of Medicine, National Institutes of Health.</p><p>Nishihara S, Angata K, Aoki-Kinoshita KF, et al., editors. Glycoscience Protocols (GlycoPODv2) [Internet]. Saitama (JP): Japan Consortium for Glycobiology and Glycotechnology; 2021-. </p></div></div></div>
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<div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><h1 id="_NBK593933_"><span class="title" itemprop="name">Conversion of pyridylamino sugar chains to corresponding reducing sugar chains</span></h1><div class="contrib half_rhythm"><span itemprop="author">Shin-ichi Nakakita</span>, Doctor of Science, Ph.D.<div class="affiliation small">Kagawa University<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="pj.ca.u-awagak.dem@atikakan" class="oemail">pj.ca.u-awagak.dem@atikakan</a></div></div><div class="small">Corresponding author.</div></div><p class="small">Created: <span itemprop="datePublished">August 24, 2021</span>; Last Revision: <span itemprop="dateModified">March 21, 2022</span>.</p></div><div class="body-content whole_rhythm" itemprop="text"><div id="g128-pyridylamino.Introduction"><h2 id="_g128-pyridylamino_Introduction_">Introduction</h2><p>Pyridylamino (PA) saccharides can be converted into the corresponding reducing sugar chains using a two-step process (<a class="figpopup" href="/books/NBK593933/figure/g128-pyridylamino.F1/?report=objectonly" target="object" rid-figpopup="figg128pyridylaminoF1" rid-ob="figobg128pyridylaminoF1">Figure 1</a>). The first step is its conversion into 1-amino-l-deoxy derivatives, and the second is its conversion into the corresponding reducing sugar chains using the Sommelet reaction (<a class="bk_pop" href="#g128-pyridylamino.REF.1">1</a>, <a class="bk_pop" href="#g128-pyridylamino.REF.2">2</a>).</p></div><div id="g128-pyridylamino.Protocol"><h2 id="_g128-pyridylamino_Protocol_">Protocol</h2><p>In this chapter, the protocol for converting PA sugar chains into reducing sugar chains will be described.</p><div id="g128-pyridylamino.Materials"><h3>Materials</h3><p>1. Palladium (Wako Pure Chemical Industries, Ltd., Osaka, Japan)</p><p>2. Hexamethylenetetramine (Wako Pure Chemical Industries Ltd.)</p><p>3. Hydrazine anhydrous (Tokyo Chemical Industry Co., Ltd., Tokyo, Japan)</p></div><div id="g128-pyridylamino.Instruments"><h3>Instruments</h3><p>1. Speed Vac Concentrator (Thermo Fisher Scientific Inc., Waltham, MA)</p><p>2. Block incubator (Astec Co., Ltd., Fukuoka, Japan)</p><p>3. Rotary oil pump connected to cold trap (Yamato Scientific Co., Ltd., Tokyo, Japan)</p><p>4. Hydrogen Generator (GL-Science, Tokyo, Japan)</p></div><div id="g128-pyridylamino.Methods"><h3>Methods</h3><dl class="temp-labeled-list"><dt>1.</dt><dd><p class="no_top_margin">Preparation of 1-amino-1-deoxy derivative from pyridylamino saccharide</p><dl class="temp-labeled-list"><dt>a.</dt><dd><p class="no_top_margin">Lyophilized PA saccharide (>1 nmol).</p></dd><dt>b.</dt><dd><p class="no_top_margin">Put it in a test tube.</p></dd><dt>c.</dt><dd><p class="no_top_margin">Add 1 mL of 0.1% Acetic acid solution.</p></dd><dt>d.</dt><dd><p class="no_top_margin">Mix it well.</p></dd><dt>e.</dt><dd><p class="no_top_margin">Add Palladium black (3 mg) (<i>see</i>
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<b>Note 1</b>).</p></dd><dt>f.</dt><dd><p class="no_top_margin">Reduce it using hydrogen gas at atmospheric pressure and at room temperature for 3 h.</p></dd><dt>g.</dt><dd><p class="no_top_margin">Filtrate by Milex filter (0.22 μM).</p></dd><dt>h.</dt><dd><p class="no_top_margin">Evaporate to dryness.</p></dd><dt>i.</dt><dd><p class="no_top_margin">Add 0.2 mL of anhydrous hydrazine (<i>see</i>
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<b>Note 2</b>).</p></dd><dt>j.</dt><dd><p class="no_top_margin">Heat it in a sealed tube at 70°C for 2 min.</p></dd><dt>k.</dt><dd><p class="no_top_margin">Remove excess hydrazine <i>in vacuo</i>.</p></dd><dt>l.</dt><dd><p class="no_top_margin">Gel filtration on a Bio-Gel P-2 column (1.2 × 90 cm; 10 mM acetic acid).</p></dd><dt>m.</dt><dd><p class="no_top_margin">Concentrate Ninhydrin positive fractions and lyophilized.</p></dd></dl></dd><dt>2.</dt><dd><p class="no_top_margin">Conversion of 1-amino-l-deoxy derivative into reducing saccharide (Sommelet reaction)</p><dl class="temp-labeled-list"><dt>a.</dt><dd><p class="no_top_margin">1-Amino-1-deoxy derivative (about 1 nmol/5 μL of water) is put in a test tube.</p></dd><dt>b.</dt><dd><p class="no_top_margin">Add 8 μL of saturated hexamethylenetetramine aqueous solution.</p></dd><dt>c.</dt><dd><p class="no_top_margin">Add 1.5 μL of 50% acetic acid aqueous solution (pH of the mixed reaction solution is 4.5).</p></dd><dt>d.</dt><dd><p class="no_top_margin">Heat it in a sealed tube at 100°C for 45 min.</p></dd><dt>e.</dt><dd><p class="no_top_margin">Add 100 μL of water.</p></dd><dt>f.</dt><dd><p class="no_top_margin">Concentrate to about 20 μL with a Speed Vac concentrator to remove volatile reagents.</p></dd><dt>g.</dt><dd><p class="no_top_margin">Add 200 μL of water.</p></dd><dt>h.</dt><dd><p class="no_top_margin">Apply to a TOYOPAK ODS cartridge.</p></dd><dt>i.</dt><dd><p class="no_top_margin">Wash with 600 μL of water.</p></dd><dt>j.</dt><dd><p class="no_top_margin">Collect eluate and washings.</p></dd><dt>k.</dt><dd><p class="no_top_margin">Add 0.6 g of Dowex 50W X2 (H<sup>+</sup>).</p></dd><dt>l.</dt><dd><p class="no_top_margin">Pour it into a small glass column.</p></dd><dt>m.</dt><dd><p class="no_top_margin">Wash with 3 column volumes of water.</p></dd><dt>n.</dt><dd><p class="no_top_margin">Collect eluate and washings, concentrate, and freeze-dry.</p></dd></dl></dd></dl></div><div id="g128-pyridylamino.Notes"><h3>Notes</h3><p>1. Palladium black may ignite when dry; thus, store it in water after use.</p><p>2. Hydrazine anhydrous is a highly toxic toxin. Wear protective glasses and gloves when using it.</p><p>3. Discussion</p><p>This method clearly indicates that 1-amino-l-deoxy sugars can be converted into corresponding sugar chains with reducing power using the Sommelet reaction.</p></div></div><div id="g128-pyridylamino.References"><h2 id="_g128-pyridylamino_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="g128-pyridylamino.REF.1">Takahashi C, Nakakita S, Hase S. Conversion of pyridylamino sugar chains to corresponding reducing sugar chains. <span><span class="ref-journal">J Biochem. </span>2003 Jul;<span class="ref-vol">134</span>(1):51–5.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12944370" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12944370</span></a>] [<a href="http://dx.crossref.org/10.1093/jb/mvg112" ref="pagearea=cite-ref&targetsite=external&targetcat=link&targettype=uri">CrossRef</a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="g128-pyridylamino.REF.2">Sommelet M. Sur un mode de décomposition des halogénoalcoylates d'hexaméthylène – tétramine. <span><span class="ref-journal">Compt Rend. </span>1913;<span class="ref-vol">157</span>:852–854.</span></div></dd></dl></div><h2 id="NBK593933_footnotes">Footnotes</h2><dl class="temp-labeled-list small"><dt></dt><dd><div id="g128-pyridylamino.FN1"><p class="no_top_margin">The authors declare no competing or financial interests.</p></div></dd></dl><div class="bk_prnt_sctn"><h2>Figures</h2><div class="whole_rhythm bk_prnt_obj bk_first_prnt_obj"><div id="g128-pyridylamino.F1" class="figure bk_fig"><div class="graphic"><img src="/books/NBK593933/bin/g128-pyridylamino-Image001.jpg" alt="Figure 1: . Scheme for the conversion of a pyridylamino sugar chain into a free sugar chain." /></div><h3><span class="label">Figure 1: </span></h3><div class="caption"><p>Scheme for the conversion of a pyridylamino sugar chain into a free sugar chain.</p></div></div></div></div><div id="bk_toc_contnr"></div></div></div>
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<div class="post-content"><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a><p class="small">Licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 4.0 Unported license. To view a copy of this license, visit <a href="http://creativecommons.org/licenses/by-nc-nd/4.0/" ref="pagearea=meta&targetsite=external&targetcat=link&targettype=uri">http://creativecommons.org/licenses/by-nc-nd/4.0/</a>.</p></div><div class="small"><span class="label">Bookshelf ID: NBK593933</span><span class="label">PMID: <a href="https://pubmed.ncbi.nlm.nih.gov/37590670" title="PubMed record of this page" ref="pagearea=meta&targetsite=entrez&targetcat=link&targettype=pubmed">37590670</a></span></div><div style="margin-top:2em" class="bk_noprnt"><a class="bk_cntns" href="/books/n/glycopodv2/">Contents</a><div class="pagination bk_noprnt"><a class="active page_link prev" href="/books/n/glycopodv2/g127-Alcianblue/" title="Previous page in this title">< Prev</a><a class="active page_link next" href="/books/n/glycopodv2/g129-methanolysis/" title="Next page in this title">Next ></a></div></div></div></div>
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