Access to Antigens Related to Anthrose Using Pivotal Cyclic Sulfite/Sulfate Intermediates

Anthrose is the upstream terminal unit of the tetrasaccharide side chain from a major glycoprotein of Bacillus anthracis exosporium and is part of important antigenic determinants. A novel entry to anthrose-containing antigens and precursors is described. The synthetic route, starting from d(+)-fuco...

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Veröffentlicht in:	Journal of organic chemistry 2011-08, Vol.76 (15), p.5985-5998
Hauptverfasser:	Milhomme, Ophélie, John, Cédric, Djedaïni-Pilard, Florence, Grandjean, Cyrille
Format:	Artikel
Sprache:	eng
Schlagworte:	Bacillus anthracis - chemistry Bacterial Proteins - chemistry Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemical Sciences Chemistry Exact sciences and technology Glycoproteins - chemistry Immunology Life Sciences Magnetic Resonance Spectroscopy Medicinal Chemistry Molecular Sequence Data Molecular Structure O Antigens - chemistry Oligosaccharides - chemical synthesis Oligosaccharides - chemistry Organic chemistry Preparations and properties Sulfites - chemical synthesis Sulfites - chemistry Vaccinology
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container_end_page	5998
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container_title	Journal of organic chemistry
container_volume	76
creator	Milhomme, Ophélie John, Cédric Djedaïni-Pilard, Florence Grandjean, Cyrille
description	Anthrose is the upstream terminal unit of the tetrasaccharide side chain from a major glycoprotein of Bacillus anthracis exosporium and is part of important antigenic determinants. A novel entry to anthrose-containing antigens and precursors is described. The synthetic route, starting from d(+)-fucose, makes use of intermediates featuring a cyclic sulfite or sulfate function which serves successively as a protecting and a leaving group.
doi_str_mv	10.1021/jo200340q
format	Article
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Nucleosides and nucleotides</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Glycoproteins - chemistry</topic><topic>Immunology</topic><topic>Life Sciences</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medicinal Chemistry</topic><topic>Molecular Sequence Data</topic><topic>Molecular Structure</topic><topic>O Antigens - chemistry</topic><topic>Oligosaccharides - chemical synthesis</topic><topic>Oligosaccharides - chemistry</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Sulfites - chemical synthesis</topic><topic>Sulfites - chemistry</topic><topic>Vaccinology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Milhomme, Ophélie</creatorcontrib><creatorcontrib>John, Cédric</creatorcontrib><creatorcontrib>Djedaïni-Pilard, Florence</creatorcontrib><creatorcontrib>Grandjean, Cyrille</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><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Milhomme, Ophélie</au><au>John, Cédric</au><au>Djedaïni-Pilard, Florence</au><au>Grandjean, Cyrille</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Access to Antigens Related to Anthrose Using Pivotal Cyclic Sulfite/Sulfate Intermediates</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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subjects	Bacillus anthracis - chemistry Bacterial Proteins - chemistry Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemical Sciences Chemistry Exact sciences and technology Glycoproteins - chemistry Immunology Life Sciences Magnetic Resonance Spectroscopy Medicinal Chemistry Molecular Sequence Data Molecular Structure O Antigens - chemistry Oligosaccharides - chemical synthesis Oligosaccharides - chemistry Organic chemistry Preparations and properties Sulfites - chemical synthesis Sulfites - chemistry Vaccinology
title	Access to Antigens Related to Anthrose Using Pivotal Cyclic Sulfite/Sulfate Intermediates
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