Literature DB >> 17566735

Synthesis of symmetrical C- and pseudo-symmetrical O-linked disaccharide analogs for arabinosyltransferase inhibitory activity in Mycobacterium tuberculosis.

Ashish K Pathak1, Vibha Pathak, James R Riordan, William J Suling, Sudagar S Gurcha, Gurdyal S Besra, Robert C Reynolds.   

Abstract

Herein we report the synthesis of symmetrical C-linked and pseudo-symmetrical O-linked disaccharides structurally related to Araf motifs present in the cell wall of MTB. Their activity in a competition-based arabinosyltransferase assay using [14C]-DPA as the glycosyl donor is also presented. In addition, in vitro inhibitory activity for the disaccharides was determined in a colorimetric broth microdilution assay system against MTB H37Ra and Mycobacterium avium.

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Year:  2007        PMID： 17566735      PMCID： PMC2699574          DOI： 10.1016/j.bmcl.2007.05.099

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  13 in total

1.  Synthesis of an arabinofuranosyl disaccharide photoaffinity probe for arabinosyltransferase activity in Mycobacterium tuberculosis.

Authors:  Ashish K Pathak; Vibha Pathak; Sudagar S Gurcha; Gurdyal S Besra; Robert C Reynolds
Journal:  Bioorg Med Chem Lett       Date:  2002-10-07       Impact factor: 2.823

2.  Studies on alpha(1-->5) linked octyl arabinofuranosyl disaccharides for mycobacterial arabinosyl transferase activity.

Authors:  A K Pathak; V Pathak; J A Maddry; W J Suling; S S Gurcha; G S Besra; R C Reynolds
Journal:  Bioorg Med Chem       Date:  2001-12       Impact factor: 3.641

3.  Synthesis of disaccharides related to the mycobacterial arabinogalactan.

Authors:  A K Pathak; V Pathak; N K Khare; J A Maddry; R C Reynolds
Journal:  Carbohydr Lett       Date:  2001

4.  Mycobacterial arabinan biosynthesis: the use of synthetic arabinoside acceptors in the development of an arabinosyl transfer assay.

Authors:  R E Lee; P J Brennan; G S Besra
Journal:  Glycobiology       Date:  1997-12       Impact factor: 4.313

5.  Synthesis of alpha- and beta-D-(1-->6)-C-Disaccharides by Wittig Olefination of Formyl C-Glycosides with Glycopyranose 6-Phosphoranes.

Authors:  Alessandro Dondoni; Helene M. Zuurmond; Alessia Boscarato
Journal:  J Org Chem       Date:  1997-11-14       Impact factor: 4.354

6.  Ethambutol-sugar hybrids as potential inhibitors of mycobacterial cell-wall biosynthesis.

Authors:  R C Reynolds; N Bansal; J Rose; J Friedrich; W J Suling; J A Maddry
Journal:  Carbohydr Res       Date:  1999-04-30       Impact factor: 2.104

Review 7.  Tuberculosis: the return of an old enemy.

Authors:  F M Collins
Journal:  Crit Rev Microbiol       Date:  1993       Impact factor: 7.624

8.  Global tuberculosis incidence and mortality during 1990-2000.

Authors:  P J Dolin; M C Raviglione; A Kochi
Journal:  Bull World Health Organ       Date:  1994       Impact factor: 9.408

Review 9.  The envelope of mycobacteria.

Authors:  P J Brennan; H Nikaido
Journal:  Annu Rev Biochem       Date:  1995       Impact factor: 23.643

10.  Synthesis of oligosaccharides as potential inhibitors of mycobacterial arabinosyltransferases. Di- and trisaccharides containing C-5 modified arabinofuranosyl residues.

Authors:  Oana M Cociorva; Todd L Lowary
Journal:  Carbohydr Res       Date:  2004-03-15       Impact factor: 2.104
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  2 in total

1.  A minimalistic approach to develop new anti-apicomplexa polyamines analogs.

Authors:  Esteban A Panozzo-Zénere; Exequiel O J Porta; Gustavo Arrizabalaga; Lucía Fargnoli; Shabana I Khan; Babu L Tekwani; Guillermo R Labadie
Journal:  Eur J Med Chem       Date:  2017-12-02       Impact factor: 6.514

2.  Synthesis of deoxygenated alpha(1-->5)-linked arabinofuranose disaccharides as substrates and inhibitors of arabinosyltransferases of Mycobacterium tuberculosis.

Authors:  Ashish K Pathak; Vibha Pathak; William J Suling; James R Riordan; Sudagar S Gurcha; Gurdyal S Besra; Robert C Reynolds
Journal:  Bioorg Med Chem       Date:  2008-11-18       Impact factor: 3.641
  2 in total

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