Synthesis of Core-class 2 O-Linked Glycopeptides: a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group
A core-class 2 tetrasaccharide-linked serine was synthesized in a convergent manner. The coupling reaction of disaccharide glycosyl donor 3 and acceptor 4 stereoselectively afforded tetrasaccharide 15, which was converted to glycosyl fluoride 20. Glycosylation of Fmoc serine allyl ester 5 with 20 pr...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2002-01, Vol.66 (9), p.1904-1914 |
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| container_end_page | 1914 |
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| container_issue | 9 |
| container_start_page | 1904 |
| container_title | Bioscience, biotechnology, and biochemistry |
| container_volume | 66 |
| creator | WATABE, Jun SINGH, Latika NAKAHARA, Yuko ITO, Yukishige HOJO, Hironobu NAKAHARA, Yoshiaki |
| description | A core-class 2 tetrasaccharide-linked serine was synthesized in a convergent manner. The coupling reaction of disaccharide glycosyl donor 3 and acceptor 4 stereoselectively afforded tetrasaccharide 15, which was converted to glycosyl fluoride 20. Glycosylation of Fmoc serine allyl ester 5 with 20 produced α- and β-glycosides in 40% and 33% yields, respectively. α-Isomer 21 was converted into 1, a useful building block for the solid-phase synthesis of glycopeptides. On the other hand, 21 was N-deprotected and condensed with hydrophobic cholestanol through a succinyl spacer. The same compound was alternatively synthesized by coupling 20 and 28. Functional group manipulation and hydrogenation afforded core 2 tetrasaccharide-cholestanol conjugate 2. |
| doi_str_mv | 10.1271/bbb.66.1904 |
| format | Article |
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The coupling reaction of disaccharide glycosyl donor 3 and acceptor 4 stereoselectively afforded tetrasaccharide 15, which was converted to glycosyl fluoride 20. Glycosylation of Fmoc serine allyl ester 5 with 20 produced α- and β-glycosides in 40% and 33% yields, respectively. α-Isomer 21 was converted into 1, a useful building block for the solid-phase synthesis of glycopeptides. On the other hand, 21 was N-deprotected and condensed with hydrophobic cholestanol through a succinyl spacer. The same compound was alternatively synthesized by coupling 20 and 28. Functional group manipulation and hydrogenation afforded core 2 tetrasaccharide-cholestanol conjugate 2.</description><identifier>ISSN: 0916-8451</identifier><identifier>EISSN: 1347-6947</identifier><identifier>DOI: 10.1271/bbb.66.1904</identifier><identifier>PMID: 12400690</identifier><language>eng</language><publisher>Tokyo: Japan Society for Bioscience, Biotechnology, and Agrochemistry</publisher><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; cholestanol ; core-class 2 ; Exact sciences and technology ; Glycopeptides - chemical synthesis ; Glycopeptides - chemistry ; glycosylation ; Hydrophobic and Hydrophilic Interactions ; Molecular Structure ; O-glycopeptide ; Organic chemistry ; Preparations and properties ; serine ; Serine - chemistry</subject><ispartof>Bioscience, biotechnology, and biochemistry, 2002-01, Vol.66 (9), p.1904-1914</ispartof><rights>2002 by Japan Society for Bioscience, Biotechnology, and Agrochemistry 2002</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c488t-41228db131cf7e8ecbc78de54f57619e91cc092f9d1128a81566f77be5a201fe3</citedby><cites>FETCH-LOGICAL-c488t-41228db131cf7e8ecbc78de54f57619e91cc092f9d1128a81566f77be5a201fe3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14444916$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12400690$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>WATABE, Jun</creatorcontrib><creatorcontrib>SINGH, Latika</creatorcontrib><creatorcontrib>NAKAHARA, Yuko</creatorcontrib><creatorcontrib>ITO, Yukishige</creatorcontrib><creatorcontrib>HOJO, Hironobu</creatorcontrib><creatorcontrib>NAKAHARA, Yoshiaki</creatorcontrib><title>Synthesis of Core-class 2 O-Linked Glycopeptides: a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group</title><title>Bioscience, biotechnology, and biochemistry</title><addtitle>Biosci Biotechnol Biochem</addtitle><description>A core-class 2 tetrasaccharide-linked serine was synthesized in a convergent manner. The coupling reaction of disaccharide glycosyl donor 3 and acceptor 4 stereoselectively afforded tetrasaccharide 15, which was converted to glycosyl fluoride 20. Glycosylation of Fmoc serine allyl ester 5 with 20 produced α- and β-glycosides in 40% and 33% yields, respectively. α-Isomer 21 was converted into 1, a useful building block for the solid-phase synthesis of glycopeptides. On the other hand, 21 was N-deprotected and condensed with hydrophobic cholestanol through a succinyl spacer. The same compound was alternatively synthesized by coupling 20 and 28. Functional group manipulation and hydrogenation afforded core 2 tetrasaccharide-cholestanol conjugate 2.</description><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>cholestanol</subject><subject>core-class 2</subject><subject>Exact sciences and technology</subject><subject>Glycopeptides - chemical synthesis</subject><subject>Glycopeptides - chemistry</subject><subject>glycosylation</subject><subject>Hydrophobic and Hydrophilic Interactions</subject><subject>Molecular Structure</subject><subject>O-glycopeptide</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>serine</subject><subject>Serine - chemistry</subject><issn>0916-8451</issn><issn>1347-6947</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkcFu1DAQhi0EotvCiTvyBS5Vth5v4iTcSgpbpJV6aDlHjjNmDV472N5W4UH6vLjaRb0wl9GMvvk1Mz8h74AtgddwMQzDUogltKx8QRawKutCtGX9kixYC6JoygpOyGmMPxnLjQpekxPgJWOiZQvyeDu7tMVoIvWadj5goayMkXJ6U2yM-4UjXdtZ-QmnZEaMn6ikn9H9mW0xBZ9QpUzcYQoySqW2MsyW3mIwDql0IzUp0qtc3stk7pF2MoTZuB9Z5Hoeg5-2fjCKdltvMSbp8vA6-P30hrzS0kZ8e8xn5PvXL3fddbG5WX_rLjeFKpsmFSVw3owDrEDpGhtUg6qbEatSV7WAFltQirVctyMAb2QDlRC6rgesJGegcXVGPh508y2_93mFfmeiQmulQ7-Pfc0FbzhnGTw_gCr4GAPqfgpml6_tgfVPNvTZhl6I_smGTL8_yu6HHY7P7PHvGfhwBGRU0uognTLxmStzZPMyJw6ccdqHnXzwwY59krP14d_Q6n8b_AXBaaTN</recordid><startdate>20020101</startdate><enddate>20020101</enddate><creator>WATABE, Jun</creator><creator>SINGH, Latika</creator><creator>NAKAHARA, Yuko</creator><creator>ITO, Yukishige</creator><creator>HOJO, Hironobu</creator><creator>NAKAHARA, Yoshiaki</creator><general>Japan Society for Bioscience, Biotechnology, and Agrochemistry</general><general>Japan Society for Bioscience Biotechnology and Agrochemistry</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>20020101</creationdate><title>Synthesis of Core-class 2 O-Linked Glycopeptides: a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group</title><author>WATABE, Jun ; SINGH, Latika ; NAKAHARA, Yuko ; ITO, Yukishige ; HOJO, Hironobu ; NAKAHARA, Yoshiaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c488t-41228db131cf7e8ecbc78de54f57619e91cc092f9d1128a81566f77be5a201fe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>cholestanol</topic><topic>core-class 2</topic><topic>Exact sciences and technology</topic><topic>Glycopeptides - chemical synthesis</topic><topic>Glycopeptides - chemistry</topic><topic>glycosylation</topic><topic>Hydrophobic and Hydrophilic Interactions</topic><topic>Molecular Structure</topic><topic>O-glycopeptide</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>serine</topic><topic>Serine - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>WATABE, Jun</creatorcontrib><creatorcontrib>SINGH, Latika</creatorcontrib><creatorcontrib>NAKAHARA, Yuko</creatorcontrib><creatorcontrib>ITO, Yukishige</creatorcontrib><creatorcontrib>HOJO, Hironobu</creatorcontrib><creatorcontrib>NAKAHARA, Yoshiaki</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>Bioscience, biotechnology, and biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>WATABE, Jun</au><au>SINGH, Latika</au><au>NAKAHARA, Yuko</au><au>ITO, Yukishige</au><au>HOJO, Hironobu</au><au>NAKAHARA, Yoshiaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Core-class 2 O-Linked Glycopeptides: a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group</atitle><jtitle>Bioscience, biotechnology, and biochemistry</jtitle><addtitle>Biosci Biotechnol Biochem</addtitle><date>2002-01-01</date><risdate>2002</risdate><volume>66</volume><issue>9</issue><spage>1904</spage><epage>1914</epage><pages>1904-1914</pages><issn>0916-8451</issn><eissn>1347-6947</eissn><abstract>A core-class 2 tetrasaccharide-linked serine was synthesized in a convergent manner. The coupling reaction of disaccharide glycosyl donor 3 and acceptor 4 stereoselectively afforded tetrasaccharide 15, which was converted to glycosyl fluoride 20. Glycosylation of Fmoc serine allyl ester 5 with 20 produced α- and β-glycosides in 40% and 33% yields, respectively. α-Isomer 21 was converted into 1, a useful building block for the solid-phase synthesis of glycopeptides. On the other hand, 21 was N-deprotected and condensed with hydrophobic cholestanol through a succinyl spacer. The same compound was alternatively synthesized by coupling 20 and 28. Functional group manipulation and hydrogenation afforded core 2 tetrasaccharide-cholestanol conjugate 2.</abstract><cop>Tokyo</cop><pub>Japan Society for Bioscience, Biotechnology, and Agrochemistry</pub><pmid>12400690</pmid><doi>10.1271/bbb.66.1904</doi><tpages>11</tpages></addata></record> |
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| ispartof | Bioscience, biotechnology, and biochemistry, 2002-01, Vol.66 (9), p.1904-1914 |
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| source | J-STAGE Free; MEDLINE; Oxford University Press Journals All Titles (1996-Current); Freely Accessible Japanese Titles; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry cholestanol core-class 2 Exact sciences and technology Glycopeptides - chemical synthesis Glycopeptides - chemistry glycosylation Hydrophobic and Hydrophilic Interactions Molecular Structure O-glycopeptide Organic chemistry Preparations and properties serine Serine - chemistry |
| title | Synthesis of Core-class 2 O-Linked Glycopeptides: a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group |
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