Chemical synthesis of the human blood-group P1-antigenic determinant
Condensation of known benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,6-tri-O-benzyl-beta-D- galactopyranosyl)-alpha-D-glucopyranoside with 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl chloride in dichloromethane in the presence of 2,4,6-trimethylpyridine, silver triflate, and molecular sieve...
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| Veröffentlicht in: | Carbohydrate research 1983-10, Vol.122 (2), p.201-208 |
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| creator | AMVAM ZOLLO, P.-H JACQUINET, J.-C SINAY, P |
| description | Condensation of known benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,6-tri-O-benzyl-beta-D- galactopyranosyl)-alpha-D-glucopyranoside with 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl chloride in dichloromethane in the presence of 2,4,6-trimethylpyridine, silver triflate, and molecular sieve 4A gave benzyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-(1 leads to 4)-O-(2,3,6-tri-O-benzyl-beta-D-galactopyranosyl)-(1 leads to 4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside. Catalytic hydrogenolysis gave crystalline O-alpha-D-galactopyranosyl-(1 leads to 4)-O-beta-D-galactopyranosyl-(1 leads to 4)-2-acetamido-2-deoxy-alpha -D-glucopyranose, the human blood-group P1-antigenic determinant. A similar sequence of reactions was performed starting from allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside, in order to prepare a derivative of this determinant suitable for linkage to carrier molecules. |
| format | Article |
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Catalytic hydrogenolysis gave crystalline O-alpha-D-galactopyranosyl-(1 leads to 4)-O-beta-D-galactopyranosyl-(1 leads to 4)-2-acetamido-2-deoxy-alpha -D-glucopyranose, the human blood-group P1-antigenic determinant. A similar sequence of reactions was performed starting from allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside, in order to prepare a derivative of this determinant suitable for linkage to carrier molecules.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>PMID: 6200222</identifier><identifier>CODEN: CRBRAT</identifier><language>eng</language><publisher>Oxford: Elsevier Science</publisher><subject>Blood Group Antigens - immunology ; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; Epitopes ; Exact sciences and technology ; Humans ; Indicators and Reagents ; Magnetic Resonance Spectroscopy ; Oligosaccharides - chemical synthesis ; Organic chemistry ; P Blood-Group System - immunology ; Preparations and properties ; Structure-Activity Relationship ; Trisaccharides - chemical synthesis</subject><ispartof>Carbohydrate research, 1983-10, Vol.122 (2), p.201-208</ispartof><rights>1984 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9338613$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6200222$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>AMVAM ZOLLO, P.-H</creatorcontrib><creatorcontrib>JACQUINET, J.-C</creatorcontrib><creatorcontrib>SINAY, P</creatorcontrib><title>Chemical synthesis of the human blood-group P1-antigenic determinant</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>Condensation of known benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,6-tri-O-benzyl-beta-D- galactopyranosyl)-alpha-D-glucopyranoside with 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl chloride in dichloromethane in the presence of 2,4,6-trimethylpyridine, silver triflate, and molecular sieve 4A gave benzyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-(1 leads to 4)-O-(2,3,6-tri-O-benzyl-beta-D-galactopyranosyl)-(1 leads to 4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside. Catalytic hydrogenolysis gave crystalline O-alpha-D-galactopyranosyl-(1 leads to 4)-O-beta-D-galactopyranosyl-(1 leads to 4)-2-acetamido-2-deoxy-alpha -D-glucopyranose, the human blood-group P1-antigenic determinant. A similar sequence of reactions was performed starting from allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside, in order to prepare a derivative of this determinant suitable for linkage to carrier molecules.</description><subject>Blood Group Antigens - immunology</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Epitopes</subject><subject>Exact sciences and technology</subject><subject>Humans</subject><subject>Indicators and Reagents</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Oligosaccharides - chemical synthesis</subject><subject>Organic chemistry</subject><subject>P Blood-Group System - immunology</subject><subject>Preparations and properties</subject><subject>Structure-Activity Relationship</subject><subject>Trisaccharides - chemical synthesis</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9j09Lw0AQxRdRaq1-BGEP4i2wf5LZ3aNUrUJBDz14C5Nk0q4km5hNDv32Bgye3rz3fgy8C7aW1ugkVfB1ydZCCJuAktk1u4nxe7YCDKzYCpQQSqk1e96eqPUlNjyew3ii6CPvaj5f_DS1GHjRdF2VHIdu6vmnTDCM_kjBl7yikYbWhzm5ZVc1NpHuFt2ww-vLYfuW7D9279unfdJbpRKXOucEpFIp5zA1RQWCTE0gqrQyaLUDhWAdGY0KCl1aMgKzOsuwAJlJvWGPf2_7ofuZKI5562NJTYOBuinmVljjHOgZvF_AqWipyvvBtzic82X13D8sPcZ5ej1gKH38x5zWFqTWv3FzX6w</recordid><startdate>19831028</startdate><enddate>19831028</enddate><creator>AMVAM ZOLLO, P.-H</creator><creator>JACQUINET, J.-C</creator><creator>SINAY, P</creator><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>7X8</scope></search><sort><creationdate>19831028</creationdate><title>Chemical synthesis of the human blood-group P1-antigenic determinant</title><author>AMVAM ZOLLO, P.-H ; JACQUINET, J.-C ; SINAY, P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p822-9499906412299a47bd60e7fe60d4d7a83962a689e73a26b3c8e70a5f55ab61513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1983</creationdate><topic>Blood Group Antigens - immunology</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Epitopes</topic><topic>Exact sciences and technology</topic><topic>Humans</topic><topic>Indicators and Reagents</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Oligosaccharides - chemical synthesis</topic><topic>Organic chemistry</topic><topic>P Blood-Group System - immunology</topic><topic>Preparations and properties</topic><topic>Structure-Activity Relationship</topic><topic>Trisaccharides - chemical synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>AMVAM ZOLLO, P.-H</creatorcontrib><creatorcontrib>JACQUINET, J.-C</creatorcontrib><creatorcontrib>SINAY, P</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>MEDLINE - Academic</collection><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>AMVAM ZOLLO, P.-H</au><au>JACQUINET, J.-C</au><au>SINAY, P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical synthesis of the human blood-group P1-antigenic determinant</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>1983-10-28</date><risdate>1983</risdate><volume>122</volume><issue>2</issue><spage>201</spage><epage>208</epage><pages>201-208</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><coden>CRBRAT</coden><abstract>Condensation of known benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,6-tri-O-benzyl-beta-D- galactopyranosyl)-alpha-D-glucopyranoside with 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl chloride in dichloromethane in the presence of 2,4,6-trimethylpyridine, silver triflate, and molecular sieve 4A gave benzyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-(1 leads to 4)-O-(2,3,6-tri-O-benzyl-beta-D-galactopyranosyl)-(1 leads to 4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside. Catalytic hydrogenolysis gave crystalline O-alpha-D-galactopyranosyl-(1 leads to 4)-O-beta-D-galactopyranosyl-(1 leads to 4)-2-acetamido-2-deoxy-alpha -D-glucopyranose, the human blood-group P1-antigenic determinant. A similar sequence of reactions was performed starting from allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside, in order to prepare a derivative of this determinant suitable for linkage to carrier molecules.</abstract><cop>Oxford</cop><pub>Elsevier Science</pub><pmid>6200222</pmid><tpages>8</tpages></addata></record> |
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| subjects | Blood Group Antigens - immunology Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Epitopes Exact sciences and technology Humans Indicators and Reagents Magnetic Resonance Spectroscopy Oligosaccharides - chemical synthesis Organic chemistry P Blood-Group System - immunology Preparations and properties Structure-Activity Relationship Trisaccharides - chemical synthesis |
| title | Chemical synthesis of the human blood-group P1-antigenic determinant |
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