Chemoenzymatic synthesis of 2-azidoethyl-ganglio-oligosaccharides GD3, GT3, GM2, GD2, GT2, GM1, and GD1a

We have synthesized several ganglio-oligosaccharide structures using glycosyltransferases from Campylobacter jejuni. The enzymes, α-(2→3/8)-sialyltransferase (Cst-II), β-(1→4)- N-acetylgalactosaminyltransferase (CgtA), and β-(1→3)-galactosyltransferase (CgtB), were produced in large-scale fermentati...

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Veröffentlicht in:	Carbohydrate research 2005-09, Vol.340 (12), p.1963-1972
Hauptverfasser:	Blixt, Ola, Vasiliu, Daniela, Allin, Kirk, Jacobsen, Nathan, Warnock, Dawn, Razi, Nahid, Paulson, James C., Bernatchez, Stéphane, Gilbert, Michel, Wakarchuk, Warren
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Schlagworte:	Chemoenzymatic Escherichia coli - enzymology G(M2) Ganglioside - chemical synthesis Galactosyltransferases - metabolism Ganglioside Gangliosides - chemical synthesis Glycosyltransferase Lactosylceramides - chemical synthesis N-Acetylgalactosaminyltransferases - metabolism Oligosaccharide Sialyltransferases - metabolism Substrate Specificity Synthesis
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container_end_page	1972
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container_title	Carbohydrate research
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creator	Blixt, Ola Vasiliu, Daniela Allin, Kirk Jacobsen, Nathan Warnock, Dawn Razi, Nahid Paulson, James C. Bernatchez, Stéphane Gilbert, Michel Wakarchuk, Warren
description	We have synthesized several ganglio-oligosaccharide structures using glycosyltransferases from Campylobacter jejuni. The enzymes, α-(2→3/8)-sialyltransferase (Cst-II), β-(1→4)- N-acetylgalactosaminyltransferase (CgtA), and β-(1→3)-galactosyltransferase (CgtB), were produced in large-scale fermentation from Escherichia coli and further characterized based on their acceptor specificities. 2-Azidoethyl-glycosides corresponding to the oligosaccharides of GD3 (α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→4)-β- D-Glc p-), GT3 (α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→4)-β- D-Glc p-), GM2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), GD2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), GT2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), and GM1 (β- D-Gal p-(1→3)-β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-) were synthesized in high yields (gram-scale). In addition, a mammalian α-(2→3)-sialyltransferase (ST3Gal I) was used to sialylate GM1 and generate GD1a (α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→3)-β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-) oligosaccharide. We also cloned and expressed a rat UDP- N-acetylglucosamine-4′epimerase (GalNAcE) in E. coli AD202 cells for cost saving in situ conversion of less expensive UDP-GlcNAc to UDP-GalNAc.
doi_str_mv	10.1016/j.carres.2005.06.008
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The enzymes, α-(2→3/8)-sialyltransferase (Cst-II), β-(1→4)- N-acetylgalactosaminyltransferase (CgtA), and β-(1→3)-galactosyltransferase (CgtB), were produced in large-scale fermentation from Escherichia coli and further characterized based on their acceptor specificities. 2-Azidoethyl-glycosides corresponding to the oligosaccharides of GD3 (α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→4)-β- D-Glc p-), GT3 (α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→4)-β- D-Glc p-), GM2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), GD2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), GT2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), and GM1 (β- D-Gal p-(1→3)-β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-) were synthesized in high yields (gram-scale). In addition, a mammalian α-(2→3)-sialyltransferase (ST3Gal I) was used to sialylate GM1 and generate GD1a (α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→3)-β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-) oligosaccharide. We also cloned and expressed a rat UDP- N-acetylglucosamine-4′epimerase (GalNAcE) in E. coli AD202 cells for cost saving in situ conversion of less expensive UDP-GlcNAc to UDP-GalNAc.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/j.carres.2005.06.008</identifier><identifier>PMID: 16005859</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Chemoenzymatic ; Escherichia coli - enzymology ; G(M2) Ganglioside - chemical synthesis ; Galactosyltransferases - metabolism ; Ganglioside ; Gangliosides - chemical synthesis ; Glycosyltransferase ; Lactosylceramides - chemical synthesis ; N-Acetylgalactosaminyltransferases - metabolism ; Oligosaccharide ; Sialyltransferases - metabolism ; Substrate Specificity ; Synthesis</subject><ispartof>Carbohydrate research, 2005-09, Vol.340 (12), p.1963-1972</ispartof><rights>2005 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c426t-6b457135362d11f68dce2fa314245d93828e055f475113b84d0079ba3dcbe3183</citedby><cites>FETCH-LOGICAL-c426t-6b457135362d11f68dce2fa314245d93828e055f475113b84d0079ba3dcbe3183</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.carres.2005.06.008$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16005859$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Blixt, Ola</creatorcontrib><creatorcontrib>Vasiliu, Daniela</creatorcontrib><creatorcontrib>Allin, Kirk</creatorcontrib><creatorcontrib>Jacobsen, Nathan</creatorcontrib><creatorcontrib>Warnock, Dawn</creatorcontrib><creatorcontrib>Razi, Nahid</creatorcontrib><creatorcontrib>Paulson, James C.</creatorcontrib><creatorcontrib>Bernatchez, Stéphane</creatorcontrib><creatorcontrib>Gilbert, Michel</creatorcontrib><creatorcontrib>Wakarchuk, Warren</creatorcontrib><title>Chemoenzymatic synthesis of 2-azidoethyl-ganglio-oligosaccharides GD3, GT3, GM2, GD2, GT2, GM1, and GD1a</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>We have synthesized several ganglio-oligosaccharide structures using glycosyltransferases from Campylobacter jejuni. The enzymes, α-(2→3/8)-sialyltransferase (Cst-II), β-(1→4)- N-acetylgalactosaminyltransferase (CgtA), and β-(1→3)-galactosyltransferase (CgtB), were produced in large-scale fermentation from Escherichia coli and further characterized based on their acceptor specificities. 2-Azidoethyl-glycosides corresponding to the oligosaccharides of GD3 (α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→4)-β- D-Glc p-), GT3 (α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→4)-β- D-Glc p-), GM2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), GD2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), GT2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), and GM1 (β- D-Gal p-(1→3)-β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-) were synthesized in high yields (gram-scale). In addition, a mammalian α-(2→3)-sialyltransferase (ST3Gal I) was used to sialylate GM1 and generate GD1a (α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→3)-β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-) oligosaccharide. We also cloned and expressed a rat UDP- N-acetylglucosamine-4′epimerase (GalNAcE) in E. coli AD202 cells for cost saving in situ conversion of less expensive UDP-GlcNAc to UDP-GalNAc.</description><subject>Chemoenzymatic</subject><subject>Escherichia coli - enzymology</subject><subject>G(M2) Ganglioside - chemical synthesis</subject><subject>Galactosyltransferases - metabolism</subject><subject>Ganglioside</subject><subject>Gangliosides - chemical synthesis</subject><subject>Glycosyltransferase</subject><subject>Lactosylceramides - chemical synthesis</subject><subject>N-Acetylgalactosaminyltransferases - metabolism</subject><subject>Oligosaccharide</subject><subject>Sialyltransferases - metabolism</subject><subject>Substrate Specificity</subject><subject>Synthesis</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE9P3DAQxa2qqCyUb4BQTj2R4D-x41wqVQssSCAui8TNcuzJxqskpnYWafn0dbQr9cbljWb03oz9Q-iS4IJgIm62hdEhQCwoxrzAosBYfkMLIiuWl1S8fUcLnEa5oISforMYt6nFohI_0CkRKSN5vUDdsoPBw_i5H_TkTBb349RBdDHzbUZz_emsh6nb9_lGj5ve-dz3buOjNqbTwVmI2eqWXWer9SzPNMntLOtZnsl1pkebRkT_RCet7iNcHOs5er2_Wy8f8qeX1ePyz1Nu0qOnXDQlrwjjTFBLSCukNUBbzUhJS25rJqkEzHlbVpwQ1sjSYlzVjWbWNMCIZOfo12Hve_B_dxAnNbhooO_1CH4XlZBY1qSsk7E8GE3wMQZo1Xtwgw57RbCaCautOhBWM2GFhUo4U-zquH_XDGD_h45Ik-H3wQDplx8OgorGwWjAugBmUta7ry_8A0FAimE</recordid><startdate>20050905</startdate><enddate>20050905</enddate><creator>Blixt, Ola</creator><creator>Vasiliu, Daniela</creator><creator>Allin, Kirk</creator><creator>Jacobsen, Nathan</creator><creator>Warnock, Dawn</creator><creator>Razi, Nahid</creator><creator>Paulson, James C.</creator><creator>Bernatchez, Stéphane</creator><creator>Gilbert, Michel</creator><creator>Wakarchuk, Warren</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050905</creationdate><title>Chemoenzymatic synthesis of 2-azidoethyl-ganglio-oligosaccharides GD3, GT3, GM2, GD2, GT2, GM1, and GD1a</title><author>Blixt, Ola ; Vasiliu, Daniela ; Allin, Kirk ; Jacobsen, Nathan ; Warnock, Dawn ; Razi, Nahid ; Paulson, James C. ; Bernatchez, Stéphane ; Gilbert, Michel ; Wakarchuk, Warren</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c426t-6b457135362d11f68dce2fa314245d93828e055f475113b84d0079ba3dcbe3183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemoenzymatic</topic><topic>Escherichia coli - enzymology</topic><topic>G(M2) Ganglioside - chemical synthesis</topic><topic>Galactosyltransferases - metabolism</topic><topic>Ganglioside</topic><topic>Gangliosides - chemical synthesis</topic><topic>Glycosyltransferase</topic><topic>Lactosylceramides - chemical synthesis</topic><topic>N-Acetylgalactosaminyltransferases - metabolism</topic><topic>Oligosaccharide</topic><topic>Sialyltransferases - metabolism</topic><topic>Substrate Specificity</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Blixt, Ola</creatorcontrib><creatorcontrib>Vasiliu, Daniela</creatorcontrib><creatorcontrib>Allin, Kirk</creatorcontrib><creatorcontrib>Jacobsen, Nathan</creatorcontrib><creatorcontrib>Warnock, Dawn</creatorcontrib><creatorcontrib>Razi, Nahid</creatorcontrib><creatorcontrib>Paulson, James C.</creatorcontrib><creatorcontrib>Bernatchez, Stéphane</creatorcontrib><creatorcontrib>Gilbert, Michel</creatorcontrib><creatorcontrib>Wakarchuk, Warren</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Blixt, Ola</au><au>Vasiliu, Daniela</au><au>Allin, Kirk</au><au>Jacobsen, Nathan</au><au>Warnock, Dawn</au><au>Razi, Nahid</au><au>Paulson, James C.</au><au>Bernatchez, Stéphane</au><au>Gilbert, Michel</au><au>Wakarchuk, Warren</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemoenzymatic synthesis of 2-azidoethyl-ganglio-oligosaccharides GD3, GT3, GM2, GD2, GT2, GM1, and GD1a</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2005-09-05</date><risdate>2005</risdate><volume>340</volume><issue>12</issue><spage>1963</spage><epage>1972</epage><pages>1963-1972</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>We have synthesized several ganglio-oligosaccharide structures using glycosyltransferases from Campylobacter jejuni. The enzymes, α-(2→3/8)-sialyltransferase (Cst-II), β-(1→4)- N-acetylgalactosaminyltransferase (CgtA), and β-(1→3)-galactosyltransferase (CgtB), were produced in large-scale fermentation from Escherichia coli and further characterized based on their acceptor specificities. 2-Azidoethyl-glycosides corresponding to the oligosaccharides of GD3 (α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→4)-β- D-Glc p-), GT3 (α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→4)-β- D-Glc p-), GM2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), GD2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), GT2 (β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→8)-α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-), and GM1 (β- D-Gal p-(1→3)-β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-) were synthesized in high yields (gram-scale). In addition, a mammalian α-(2→3)-sialyltransferase (ST3Gal I) was used to sialylate GM1 and generate GD1a (α- D-Neu p5Ac-(2→3)-β- D-Gal p-(1→3)-β- D-Gal pNAc-(1→4)-[α- D-Neu p5Ac-(2→3)]-β- D-Gal p-(1→4)-β- D-Glc p-) oligosaccharide. We also cloned and expressed a rat UDP- N-acetylglucosamine-4′epimerase (GalNAcE) in E. coli AD202 cells for cost saving in situ conversion of less expensive UDP-GlcNAc to UDP-GalNAc.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>16005859</pmid><doi>10.1016/j.carres.2005.06.008</doi><tpages>10</tpages></addata></record>
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subjects	Chemoenzymatic Escherichia coli - enzymology G(M2) Ganglioside - chemical synthesis Galactosyltransferases - metabolism Ganglioside Gangliosides - chemical synthesis Glycosyltransferase Lactosylceramides - chemical synthesis N-Acetylgalactosaminyltransferases - metabolism Oligosaccharide Sialyltransferases - metabolism Substrate Specificity Synthesis
title	Chemoenzymatic synthesis of 2-azidoethyl-ganglio-oligosaccharides GD3, GT3, GM2, GD2, GT2, GM1, and GD1a
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