Literature DB >> 18436197

Synthesis of spacer-equipped di-, tri-, and the tetrasaccharide fragments of the deacetylated O-PS1 of Citrobacter gillenii O9a,9b, and a related pentasaccharide.

Rina Saksena1, Anatoli Chernyak, Pavol Kovác.   

Abstract

The title rhamnooligosaccharides [alpha-D-Rhap4NAc-(1-->3)-alpha-D-Rhap4NAc-1-O-(CH(2))(5)COOMe, alpha-D-Rhap4NAc-(1-->3)-alpha-D-Rhap4NAc-(1-->3)-alpha-D-Rhap4NAc-1-O-(CH(2))(5)COOMe, alpha-D-Rhap4NAc-(1-->2)-alpha-D-Rhap4NAc-(1-->3)-alpha-D-Rhap4NAc-(1-->3)-alpha-D-Rhap4NAc-1-O-(CH(2))(5)COOMe, and alpha-D-Rhap4NAc-(1-->3)-alpha-D-Rhap4NAc-(1-->2)-alpha-D-Rhap4NAc-(1-->3)-alpha-D-Rhap4NAc-(1-->3)-alpha-D-Rhap4NAc-1-O-(CH(2))(5)COOMe] were synthesized in a stepwise fashion from 5-methoxycarbonylpentyl 4-azido-4,6-dideoxy-2-O-benzyl-alpha-D-mannopyranoside and orthogonally protected 1-thioglycoside glycosyl donors. The amorphous, final products were fully characterized as corresponding per-O-acetyl derivatives.

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Year:  2008        PMID： 18436197      PMCID： PMC2570536          DOI： 10.1016/j.carres.2008.03.037

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  16 in total

1.  Reduction of azides under conditions of desorption-chemical ionization or fast-atom-bombardment mass-spectrometry.

Authors:  J M Peltier; R W Smith; D B MacLean; W A Szarek
Journal:  Carbohydr Res       Date:  1990-10-15       Impact factor: 2.104

2.  An improved synthesis of D-perosamine and some derivatives.

Authors:  M J Eis; B Ganem
Journal:  Carbohydr Res       Date:  1988-05-15       Impact factor: 2.104

3.  Conjugating oligosaccharides to proteins by squaric acid diester chemistry: rapid monitoring of the progress of conjugation, and recovery of the unused ligand.

Authors:  A Chernyak; A Karavanov; Y Ogawa; P Kovác
Journal:  Carbohydr Res       Date:  2001-02-28       Impact factor: 2.104

4.  Antigenic relationships of the lipopolysaccharides of Escherichia hermannii strains with those of Escherichia coli O157:H7, Brucella melitensis, and Brucella abortus.

Authors:  M B Perry; D R Bundle
Journal:  Infect Immun       Date:  1990-05       Impact factor: 3.441

5.  Induction of protective immunity by synthetic Vibrio cholerae hexasaccharide derived from V. cholerae O1 Ogawa lipopolysaccharide bound to a protein carrier.

Authors:  Anatoly Chernyak; Seiichi Kondo; Terri K Wade; Michael D Meeks; Pedro M Alzari; Jean-Michel Fournier; Ronald K Taylor; Pavol Kovác; William F Wade
Journal:  J Infect Dis       Date:  2002-03-19       Impact factor: 5.226

6.  Citrobacter freundii invades and replicates in human brain microvascular endothelial cells.

Authors:  J L Badger; M F Stins; K S Kim
Journal:  Infect Immun       Date:  1999-08       Impact factor: 3.441

7.  Stereoselective syntheses of a di-, tri-, and tetra-saccharide fragment of Shigella dysenteriae type 1 O-antigen using 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranosyl chloride as a glycosyl donor.

Authors:  V Pavliak; P Kovác; C P Glaudemans
Journal:  Carbohydr Res       Date:  1992-05-14       Impact factor: 2.104

8.  One-pot preparation of a series of glycoconjugates with predetermined antigen-carrier ratio from oligosaccharides that mimic the O-PS of Vibrio cholerae O:1, serotype Ogawa.

Authors:  Rina Saksena; Xingquan Ma; Pavol Kovác
Journal:  Carbohydr Res       Date:  2003-11-14       Impact factor: 2.104

9.  Neoglycoconjugates from synthetic tetra- and hexasaccharides that mimic the terminus of the O-PS of Vibrio cholerae O:1, serotype Inaba.

Authors:  Xingquan Ma; Rina Saksena; Anatoly Chernyak; Pavol Kovác
Journal:  Org Biomol Chem       Date:  2003-03-07       Impact factor: 3.876

10.  Synthesis of antigenic determinants of the Brucella A antigen, utilizing methyl 4-azido-4,6-dideoxy-alpha-D-mannopyranoside efficiently derived from D-mannose.

Authors:  D R Bundle; M Gerken; T Peters
Journal:  Carbohydr Res       Date:  1988-03-15       Impact factor: 2.104
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