Synthesis of linear-B saccharopeptides via enzymatic galactosylation of non-natural glucosamide acceptors
A series of d- and l-glycopyranuronic acids are coupled to glucosamines to give saccharopeptides. These ‘disaccharides’, in which the acetyl moiety of the natural N-acetyl-glucosamine is replaced by various sugar acids, turned out to be surprisingly good substrates for β(1-4)-galactosyl-transferase...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2001-07, Vol.9 (7), p.1857-1869 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Schwardt, Oliver Baisch, Gabi Öhrlein, Reinhold |
| description | A series of
d- and
l-glycopyranuronic acids are coupled to glucosamines to give saccharopeptides. These ‘disaccharides’, in which the acetyl moiety of the natural
N-acetyl-glucosamine is replaced by various sugar acids, turned out to be surprisingly good substrates for β(1-4)-galactosyl-transferase and α(1-3)-galactosyl-transferase. The enzymes transfer successively two galactose units from the donor UDP-galactose onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to give linear-B saccharopeptides.
β(1-4)- and recombinant α(1-3)-galactosyl-transferases are used on a preparative scale to glycosylate a series of saccharopeptides to give non-natural linear-B trisaccharide analogues. |
| doi_str_mv | 10.1016/S0968-0896(01)00086-4 |
| format | Article |
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d- and
l-glycopyranuronic acids are coupled to glucosamines to give saccharopeptides. These ‘disaccharides’, in which the acetyl moiety of the natural
N-acetyl-glucosamine is replaced by various sugar acids, turned out to be surprisingly good substrates for β(1-4)-galactosyl-transferase and α(1-3)-galactosyl-transferase. The enzymes transfer successively two galactose units from the donor UDP-galactose onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to give linear-B saccharopeptides.
β(1-4)- and recombinant α(1-3)-galactosyl-transferases are used on a preparative scale to glycosylate a series of saccharopeptides to give non-natural linear-B trisaccharide analogues.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/S0968-0896(01)00086-4</identifier><identifier>PMID: 11425588</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Amides - chemistry ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Carbohydrates - chemical synthesis ; Carbohydrates - chemistry ; Fundamental and applied biological sciences. Psychology ; Galactose - chemistry ; Galactosyltransferases - chemistry ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Methods. Procedures. Technologies ; N-Acetyllactosamine Synthase - chemistry ; Peptides - chemical synthesis ; Peptides - chemistry</subject><ispartof>Bioorganic & medicinal chemistry, 2001-07, Vol.9 (7), p.1857-1869</ispartof><rights>2001 Elsevier Science Ltd</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c305t-77b477b15265419b47e13166a069b576e39fd135c9362d2768c667ff464c4df3</citedby><cites>FETCH-LOGICAL-c305t-77b477b15265419b47e13166a069b576e39fd135c9362d2768c667ff464c4df3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0968-0896(01)00086-4$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1041726$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11425588$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Schwardt, Oliver</creatorcontrib><creatorcontrib>Baisch, Gabi</creatorcontrib><creatorcontrib>Öhrlein, Reinhold</creatorcontrib><title>Synthesis of linear-B saccharopeptides via enzymatic galactosylation of non-natural glucosamide acceptors</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of
d- and
l-glycopyranuronic acids are coupled to glucosamines to give saccharopeptides. These ‘disaccharides’, in which the acetyl moiety of the natural
N-acetyl-glucosamine is replaced by various sugar acids, turned out to be surprisingly good substrates for β(1-4)-galactosyl-transferase and α(1-3)-galactosyl-transferase. The enzymes transfer successively two galactose units from the donor UDP-galactose onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to give linear-B saccharopeptides.
β(1-4)- and recombinant α(1-3)-galactosyl-transferases are used on a preparative scale to glycosylate a series of saccharopeptides to give non-natural linear-B trisaccharide analogues.</description><subject>Amides - chemistry</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Carbohydrates - chemical synthesis</subject><subject>Carbohydrates - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Galactose - chemistry</subject><subject>Galactosyltransferases - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Methods. Procedures. Technologies</subject><subject>N-Acetyllactosamine Synthase - chemistry</subject><subject>Peptides - chemical synthesis</subject><subject>Peptides - chemistry</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhi0EokvhJ4ByQAgOAU_sOMkJQcWXVIlDe7dmnUlr5NiLJ6m0_Hq83RVw42BZIz3v6_EjxHOQb0GCeXclB9PXsh_MawlvpJS9qfUDsQFtdK3UAA_F5g9yJp4w_yhQowd4LM4AdNO2fb8R_mofl1tiz1WaquAjYa4_VozO3WJOO9otfiSu7jxWFH_tZ1y8q24woFsS70MZUzxEY4p1xGXNGKqbsLrEOJdkVYpKR8r8VDyaMDA9O93n4vrzp-uLr_Xl9y_fLj5c1k7Jdqm7bqvLgbYxrYahDAQKjEFphm3bGVLDNIJq3aBMMzad6Z0x3TSVbzs9TupcvDrW7nL6uRIvdvbsKASMlFa2XZGiVd8VsD2CLifmTJPdZT9j3luQ9qDY3iu2B39Wgr1XbHXJvTg9sG5nGv-mTk4L8PIEIDsMU8boPP_TrqFrTMHeHzEqMu48ZcvOU3Q0-kxusWPy_9nkN_ZfmR4</recordid><startdate>200107</startdate><enddate>200107</enddate><creator>Schwardt, Oliver</creator><creator>Baisch, Gabi</creator><creator>Öhrlein, Reinhold</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><scope>IQODW</scope><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>200107</creationdate><title>Synthesis of linear-B saccharopeptides via enzymatic galactosylation of non-natural glucosamide acceptors</title><author>Schwardt, Oliver ; Baisch, Gabi ; Öhrlein, Reinhold</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c305t-77b477b15265419b47e13166a069b576e39fd135c9362d2768c667ff464c4df3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Amides - chemistry</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Carbohydrates - chemical synthesis</topic><topic>Carbohydrates - chemistry</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Galactose - chemistry</topic><topic>Galactosyltransferases - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Methods. Procedures. Technologies</topic><topic>N-Acetyllactosamine Synthase - chemistry</topic><topic>Peptides - chemical synthesis</topic><topic>Peptides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schwardt, Oliver</creatorcontrib><creatorcontrib>Baisch, Gabi</creatorcontrib><creatorcontrib>Öhrlein, Reinhold</creatorcontrib><collection>Pascal-Francis</collection><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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Schwardt, Oliver</au><au>Baisch, Gabi</au><au>Öhrlein, Reinhold</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of linear-B saccharopeptides via enzymatic galactosylation of non-natural glucosamide acceptors</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2001-07</date><risdate>2001</risdate><volume>9</volume><issue>7</issue><spage>1857</spage><epage>1869</epage><pages>1857-1869</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A series of
d- and
l-glycopyranuronic acids are coupled to glucosamines to give saccharopeptides. These ‘disaccharides’, in which the acetyl moiety of the natural
N-acetyl-glucosamine is replaced by various sugar acids, turned out to be surprisingly good substrates for β(1-4)-galactosyl-transferase and α(1-3)-galactosyl-transferase. The enzymes transfer successively two galactose units from the donor UDP-galactose onto these acceptor substrates, despite the far reaching alterations, regio- and stereospecifically in the expected manner to give linear-B saccharopeptides.
β(1-4)- and recombinant α(1-3)-galactosyl-transferases are used on a preparative scale to glycosylate a series of saccharopeptides to give non-natural linear-B trisaccharide analogues.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>11425588</pmid><doi>10.1016/S0968-0896(01)00086-4</doi><tpages>13</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Bioorganic & medicinal chemistry, 2001-07, Vol.9 (7), p.1857-1869 |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Amides - chemistry Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Carbohydrates - chemical synthesis Carbohydrates - chemistry Fundamental and applied biological sciences. Psychology Galactose - chemistry Galactosyltransferases - chemistry Magnetic Resonance Spectroscopy Mass Spectrometry Methods. Procedures. Technologies N-Acetyllactosamine Synthase - chemistry Peptides - chemical synthesis Peptides - chemistry |
| title | Synthesis of linear-B saccharopeptides via enzymatic galactosylation of non-natural glucosamide acceptors |
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