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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="_NBK593861_"><span class="title" itemprop="name">Metabolic labeling of glycans by radioactive sugars</span></h1><div class="contrib half_rhythm"><span itemprop="author">Takashi Ohkura</span>, Ph.D.<div class="affiliation small">Department of Reproductive Biology, National Institute for Child Health and Development<div><span class="email-label">Email: </span><a href="mailto:dev@null" data-email="pj.og.dhccn@kt-aruko" class="oemail">pj.og.dhccn@kt-aruko</a></div></div><div class="small">Corresponding author.</div></div><p class="small">Created: <span itemprop="datePublished">September 28, 2021</span>; Last Revision: <span itemprop="dateModified">February 3, 2022</span>.</p></div><div class="body-content whole_rhythm" itemprop="text"><div id="g124-radioactivesug.Introduction"><h2 id="_g124-radioactivesug_Introduction_">Introduction</h2><p>When cells are cultured in a medium that contains a radio-isotope-labeled monosaccharide, the sugar chains of the glycoproteins and glycolipids are metabolically radiolabeled efficiently. Although there are several constraints in using radioisotopes in the laboratory, this is a useful method because metabolically labeled glycans could be detected with high sensitivity via various analytical methods. Consequently, it becomes possible to deduce the structure of sugar chains using various chromatographic methods without a mass spectrometer; and although limited glycans could be prepared from the immunoprecipitated glycoproteins.</p></div><div id="g124-radioactivesug.Protocol"><h2 id="_g124-radioactivesug_Protocol_">Protocol</h2><p>This protocol will be described for the sequential preparations of <i>N</i>-glycans and <i>O</i>-glycans from the glycoproteins labeled by [<sup>3</sup>H]glucosamine (<a class="bk_pop" href="#g124-radioactivesug.REF.1">1</a>).</p><div id="g124-radioactivesug.Materials"><h3>Materials</h3><dl class="temp-labeled-list"><dt>1.</dt><dd><p class="no_top_margin">Glucosamine hydrochloride, D-[6-<sup>3</sup>H] (1.48~2.22 TBq/mmol; American Radiolabeled Chemicals, Inc., St. Louis, MO)</p></dd><dt>2.</dt><dd><p class="no_top_margin">Culture mediums specified for the cells with and without glucose (DMEM and RPMI-1640) are commercially available from Invitrogen/Life Technologies, Carlsbad, CA</p></dd><dt>3.</dt><dd><p class="no_top_margin">PNGase F (<i>Flavobacterium meningosepticum</i>) is commercially available from Takara-Bio Inc., Otsu, Japan; Sigma-Aldrich, St. Louis, MO (proteomics grade); and Roche Diagnostics GmbH, Mannheim, Germany</p></dd><dt>4.</dt><dd><p class="no_top_margin">Sep-Pak Vac 3 cc C18 cartridge (Waters Corp., Milford, MA)</p></dd><dt>5.</dt><dd><p class="no_top_margin">Dialyzed Fetal Calf Serum (FCS)</p></dd><dt>6.</dt><dd><p class="no_top_margin">10 mM Tris-HCl buffered saline, pH 7.4 (TBS)</p></dd><dt>7.</dt><dd><p class="no_top_margin">0.1 M KOH/2 M NaBH<sub>4</sub></p></dd><dt>8.</dt><dd><p class="no_top_margin">Acetic acid</p></dd><dt>9.</dt><dd><p class="no_top_margin">AG-50W-X8 (H<sup>+</sup>, 50–100 mesh) resin (Bio-Rad Laboratories, Hercules, CA)</p></dd><dt>10.</dt><dd><p class="no_top_margin">Centrifugal ultrafilter device (Amicon Ultra-4, 10 k; Merck Millipore, Billerica, MA)</p></dd><dt>11.</dt><dd><p class="no_top_margin">Methanol</p></dd></dl></div><div id="g124-radioactivesug.Instruments"><h3>Instruments</h3><dl class="temp-labeled-list"><dt>1.</dt><dd><p class="no_top_margin">CO<sub>2</sub> incubator</p></dd><dt>2.</dt><dd><p class="no_top_margin">Reaction incubator (100°C, 37°C, and 30°C)</p></dd><dt>3.</dt><dd><p class="no_top_margin">Liquid scintillation counter, such as MicroBeta TriLux 1450 (PerkinElmer, Waltham, MA) or LSC-6000 (Hitachi Aloka Medical, Ltd., Tokyo, Japan)</p></dd><dt>4.</dt><dd><p class="no_top_margin">Centrifugal vacuum concentrator</p></dd><dt>5.</dt><dd><p class="no_top_margin">Chromatographic systems for further analysis</p></dd></dl></div><div id="g124-radioactivesug.Methods"><h3>Methods</h3><dl class="temp-labeled-list"><dt>1.</dt><dd><p class="no_top_margin">Metabolic labeling of glycans by radioactive sugars</p><dl class="temp-labeled-list"><dt>a.</dt><dd><p class="no_top_margin">Prepare ~80% confluent cells cultured in a 10 cm dish under specified conditions.</p></dd><dt>b.</dt><dd><p class="no_top_margin">Wash once with glucose-free medium containing 2% dialyzed FCS.</p></dd><dt>c.</dt><dd><p class="no_top_margin">Replace with 4 mL of medium containing 1.85–7.4 MBq (50–200 μCi) of [<sup>3</sup>H]glucosamine, 1/10 concentration of glucose, and 2% dialyzed FCS.</p></dd><dt>d.</dt><dd><p class="no_top_margin">Incubate at 37°C for 20–24 h under 5% CO<sub>2</sub> atmosphere.</p></dd><dt>e.</dt><dd><p class="no_top_margin">Centrifuge the collected medium at 10,000 ×<i>g</i> for 10 min, and collect the supernatant.</p></dd><dt>f.</dt><dd><p class="no_top_margin">Remove the radioactive components (M.W. -10 kDa) with an ultrafiltration device (Amicon Ultra-4), change buffer to TBS, and finally concentrate to 100–200 μL.</p></dd><dt>g.</dt><dd><p class="no_top_margin">Harvest the cells in PBS using a rubber cell scraper and then centrifuge to collect cells.</p></dd></dl></dd><dt>2.</dt><dd><p class="no_top_margin">Preparation of <i>N</i>-glycans</p><dl class="temp-labeled-list"><dt>a.</dt><dd><p class="no_top_margin">Denature the packed cells or the solution obtained in (1.f) and then digest with PNGase F according to the manufacturer’s instructions at 37°C for 18 h (see section “<i>N</i>-glycanase digestion”).</p></dd><dt>b.</dt><dd><p class="no_top_margin">Heat at 100°C for 3 min, and then, separate the released <i>N</i>-glycans from the reaction mixture using ultrafiltration with milli-Q water.</p></dd><dt>c.</dt><dd><p class="no_top_margin">Apply the filtrate as obtained above in Step 2b to a Sep-Pak Vac C18 cartridge that was prewashed with methanol and milli-Q water, and the flow-through fraction was dried using a centrifugal vacuum concentrator.</p></dd></dl></dd><dt>3.</dt><dd><p class="no_top_margin">Preparation of <i>O</i>-glycans</p><dl class="temp-labeled-list"><dt>a.</dt><dd><p class="no_top_margin">Transfer the residual material (0.1–0.2 mL) of the ultrafiltration device in step (2.b) to a 1.5 mL tube, add an equal volume of 0.1 M KOH/2 M NaBH<sub>4</sub> solution, and incubate at 30°C for 15 h.</p></dd><dt>b.</dt><dd><p class="no_top_margin">Transfer the reaction mixture to a 15 mL tube and add several drops of acetic acid carefully because a large amount of H<sub>2</sub> bubbles are formed.</p></dd><dt>c.</dt><dd><p class="no_top_margin">When the bubbling ends, apply the reaction mixture to a Sep-Pac Vac C18 cartridge (3 cc), overlayered with 2 mL of AG-50W(H<sup>+</sup>) resin that was prewashed with milli-Q water, and then flushed out with 10 mL of milli-Q water.</p></dd><dt>d.</dt><dd><p class="no_top_margin">Collect the flow-through fraction and dry it in a centrifugal vacuum concentrator.</p></dd><dt>e.</dt><dd><p class="no_top_margin">Add 1 mL of methanol and dry; repeat this step twice.</p></dd></dl></dd><dt>4.</dt><dd><p class="no_top_margin">Analysis of <i>N</i>-glycans (<a class="figpopup" href="/books/NBK593861/figure/g124-radioactivesug.F1/?report=objectonly" target="object" rid-figpopup="figg124radioactivesugF1" rid-ob="figobg124radioactivesugF1">Figure 1A</a>) and <i>O</i>-glycans (<a class="figpopup" href="/books/NBK593861/figure/g124-radioactivesug.F1/?report=objectonly" target="object" rid-figpopup="figg124radioactivesugF1" rid-ob="figobg124radioactivesugF1">Figure 1B</a>)</p><dl class="temp-labeled-list"><dt>a.</dt><dd><p class="no_top_margin">Obtained <i>N</i>-glycans and <i>O</i>-glycans are subsequently available for further analysis via chromatography, such as Bio-Gel P-4 gel permeation chromatography (Bio-Rad Lab), Mono Q ion exchange column chromatography (Bio-Rad Lab), C18 reverse-phase column chromatography, Amido80 normal phase column chromatography (TOSOH BIOSCIENCE, Japan), PGC chromatography (TOSOH BIOSCIENCE), and serial lectin column chromatography (<a class="bk_pop" href="#g124-radioactivesug.REF.1">1</a>,<a class="bk_pop" href="#g124-radioactivesug.REF.2">2</a>) (<b>Notes 1–3</b>).</p></dd></dl></dd></dl></div><div id="g124-radioactivesug.Notes"><h3>Notes</h3><dl class="temp-labeled-list"><dt>1.</dt><dd><p class="no_top_margin">Labeling with [<sup>3</sup>H]glucosamine is suitable for analyzing the side chain structure of glycans biosynthesized in the cells because [<sup>3</sup>H]glucosamine shows the highest efficiency of incorporation into the cells and subsequent metabolical conversion to GlcNAc, GalNAc, and Gal of <i>N</i>-glycan and <i>O</i>-glycan.</p></dd><dt>2.</dt><dd><p class="no_top_margin">Metabolic labeling of the cultured cells with [<sup>3</sup>H]mannose for 30 min provides high-mannose-type glycans, lipid-linked oligosaccharide intermediate, and GPI intermediate (<a class="bk_pop" href="#g124-radioactivesug.REF.3">3</a>).</p></dd><dt>3.</dt><dd><p class="no_top_margin">Since the sugar chains obtained from the collected culture medium are derived from both radiolabeled secreted glycoproteins and nonlabeled glycoproteins from the supplemented FCS, the total glycan content might affect the behavior of the lectin column chromatography or other analysis.</p></dd></dl></div></div><div id="g124-radioactivesug.References"><h2 id="_g124-radioactivesug_References_">References</h2><dl class="temp-labeled-list"><dt>1.</dt><dd><div class="bk_ref" id="g124-radioactivesug.REF.1">Ohkura T, Seko A, Hara-Kuge S, Yamashita K. Occurrence of secretory glycoprotein-specific GalNAc beta 1-->4GlcNAc sequence in N-glycans in MDCK cells. <span><span class="ref-journal">J Biochem. </span>2002;<span class="ref-vol">132</span>:891–901.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/12473191" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 12473191</span></a>] [<a href="http://dx.crossref.org/10.1093/oxfordjournals.jbchem.a003302" ref="pagearea=cite-ref&targetsite=external&targetcat=link&targettype=uri">CrossRef</a>]</div></dd><dt>2.</dt><dd><div class="bk_ref" id="g124-radioactivesug.REF.2">Seko A, Ohkura T, Ideo H, Yamashita K. Novel <em>O</em>-linked glycans containing 6'-sulfo-Gal/GalNAc of MUC1 secreted from human breast cancer YMB-S cells: possible carbohydrate epitopes of KL-6(MUC1) monoclonal antibody. <span><span class="ref-journal">Glycobiology. </span>2012;<span class="ref-vol">22</span>(2):181–95.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/21880669" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21880669</span></a>] [<a href="http://dx.crossref.org/10.1093/glycob/cwr118" ref="pagearea=cite-ref&targetsite=external&targetcat=link&targettype=uri">CrossRef</a>]</div></dd><dt>3.</dt><dd><div class="bk_ref" id="g124-radioactivesug.REF.3">Fukushima K, Ohkura T, Yamashita K. Synthesis of lipid-linked oligosaccharides is dependent on the cell cycle in rat 3Y1 cells. <span><span class="ref-journal">J Biochem. </span>1997;<span class="ref-vol">121</span>:415–8.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/9133608" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 9133608</span></a>] [<a href="http://dx.crossref.org/10.1093/oxfordjournals.jbchem.a021604" ref="pagearea=cite-ref&targetsite=external&targetcat=link&targettype=uri">CrossRef</a>]</div></dd></dl></div><h2 id="NBK593861_footnotes">Footnotes</h2><dl class="temp-labeled-list small"><dt></dt><dd><div id="g124-radioactivesug.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="g124-radioactivesug.F1" class="figure bk_fig"><div class="graphic"><a href="/core/lw/2.0/html/tileshop_pmc/tileshop_pmc_inline.html?title=Figure%201%3A%20.%20N-glycans%20and%20O-glycans%20derived%20from%20%5B3H%5Dglucosamine-labeled%20Jurkat%20cells.&p=BOOKS&id=593861_g124-radioactivesug-Image001.jpg" target="tileshopwindow" class="inline_block pmc_inline_block ts_canvas img_link" title="Click on image to zoom"><div class="ts_bar small" title="Click on image to zoom"></div><img src="/books/NBK593861/bin/g124-radioactivesug-Image001.jpg" alt="Figure 1: . N-glycans and O-glycans derived from [3H]glucosamine-labeled Jurkat cells." class="tileshop" title="Click on image to zoom" /></a></div><h3><span class="label">Figure 1: </span></h3><div class="caption"><p><i>N</i>-glycans and <i>O</i>-glycans derived from [<sup>3</sup>H]glucosamine-labeled Jurkat cells.</p><p>(<i>B</i>) Released <i>O</i>-glycans are separated to neutral sugars (N) and acidic sugars (A) by ion exchange chromatography, and the acidic sugars (A) are neutralized by digestion with <i>Arthrobacter ureafaciens</i> sialidase (Nacalai Tesque, Japan) (AN). N and AN are separated using the Bio-Gel P-4 column, and the resulting peaks 1, 2, and 3 correspond to a mixture of GlcNAc<sub>OH</sub> and GalNAc<sub>OH</sub>, Gal-GalNAc<sub>OH</sub>, and Gal-(Gal-GlcNAc-)GalNAc<sub>OH</sub>, respectively. The right panels show the monosaccharide analysis patterns (Shodex SP0810 column, Japan) after acid hydrolysis of the components (<a class="bk_pop" href="#g124-radioactivesug.REF.1">1</a>-<a class="bk_pop" href="#g124-radioactivesug.REF.3">3</a>) (<b>Note 1</b>).</p><p>(<i>A</i>) <i>N</i>-glycans released from radiolabeled cells were reduced with NaBH<sub>4</sub>, and digested with sialidase, and the obtained neutral sugar chains were then separated by the Bio-Gel P-4 gel permeation chromatography. M5-M9 and L2-L6 correspond to Man<sub>5-9</sub>·GlcNAc·GlcNAc<sub>OT</sub> and (GalGlcNAc)<sub>2-6</sub>·Man<sub>3</sub>·GlcNAc·GlcNAc<sub>OT,</sub> respectively. The arrows at the top of the figure indicate the elution positions of glucose oligomers (the numbers are those of the glucose units). To deduce the glycan structure, the use of other structural analysis methods is necessary.</p></div></div></div></div><div id="bk_toc_contnr"></div></div></div>
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<span class="PAFAppResources"></span>
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<noscript><img alt="statistics" src="/stat?jsdisabled=true&ncbi_db=books&ncbi_pdid=book-part&ncbi_acc=NBK593861&ncbi_domain=glycopodv2&ncbi_report=printable&ncbi_type=fulltext&ncbi_objectid=&ncbi_pcid=/NBK593861/?report=printable&ncbi_app=bookshelf" /></noscript>
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<span id="portal-csrf-token" style="display:none" data-token="CE8B5AF87C7FFCB1_0191SID"></span>
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<script type="text/javascript" src="//static.pubmed.gov/portal/portal3rc.fcgi/4216699/js/3879255/4121861/3501987/4008961/3893018/3821238/3400083/3426610.js" snapshot="books"></script></body>
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</html> |