Literature DB >> 19691955

Synthesis of potassium (2R)-2-O-alpha-d-glucopyranosyl-(1-->6)-alpha-d-glucopyranosyl-2,3-dihydroxypropanoate a natural compatible solute.

Eva C Lourenço1, Christopher D Maycock, M Rita Ventura.   

Abstract

Ethyl 6-O-acetyl-2,3,4-tribenzyl-1-thio-d-glucopyranoside, as a mixture of anomers, was employed for the stereoselective synthesis of the potassium salt of (2R)-2-O-alpha-d-glucopyranosyl-(1-->6)-alpha-d-glucopyranosyl-2,3-dihydroxypropanoic acid (alpha-d-glucosyl-(1-->6)-alpha-d-glucosyl-(1-->2)-d-glyceric acid, GGG), a recently isolated compatible solute. The alpha-anomer was by far the major product of both glycosylation reactions using NIS/TfOH as activator.

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Year:  2009        PMID： 19691955     DOI： 10.1016/j.carres.2009.06.037

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


  9 in total

1.  Functional Characterization of the ycjQRS Gene Cluster from Escherichia coli: A Novel Pathway for the Transformation of d-Gulosides to d-Glucosides.

Authors:  Keya Mukherjee; Jamison P Huddleston; Tamari Narindoshvili; Venkatesh V Nemmara; Frank M Raushel
Journal:  Biochemistry       Date:  2019-02-20       Impact factor: 3.162

2.  Discovery of a Kojibiose Phosphorylase in Escherichia coli K-12.

Authors:  Keya Mukherjee; Tamari Narindoshvili; Frank M Raushel
Journal:  Biochemistry       Date:  2018-04-30       Impact factor: 3.162

3.  Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors:  David Crich
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

4.  Further studies on cation clock reactions in glycosylation: observation of a configuration specific intramolecular sulfenyl transfer and isolation and characterization of a tricyclic acetal.

Authors:  Min Huang; Takayuki Furukawa; Pascal Retailleau; David Crich; Luis Bohé
Journal:  Carbohydr Res       Date:  2016-04-06       Impact factor: 2.104

5.  Organic solutes in the deepest phylogenetic branches of the Bacteria: identification of α(1-6)glucosyl-α(1-2)glucosylglycerate in Persephonella marina.

Authors:  Pedro Lamosa; Marta V Rodrigues; Luís G Gonçalves; Jean Carr; Rita Ventura; Christopher Maycock; Neil D Raven; Helena Santos
Journal:  Extremophiles       Date:  2012-11-24       Impact factor: 2.395

6.  The plant Selaginella moellendorffii possesses enzymes for synthesis and hydrolysis of the compatible solutes mannosylglycerate and glucosylglycerate.

Authors:  Ana Nobre; Nuno Empadinhas; Maria Fernanda Nobre; Eva Correia Lourenço; Christopher Maycock; Maria Rita Ventura; Ana Mingote; Milton S da Costa
Journal:  Planta       Date:  2012-11-20       Impact factor: 4.116

7.  The influence of acceptor nucleophilicity on the glycosylation reaction mechanism.

Authors:  S van der Vorm; T Hansen; H S Overkleeft; G A van der Marel; J D C Codée
Journal:  Chem Sci       Date:  2016-11-09       Impact factor: 9.825

8.  Mycobacterium hassiacum recovers from nitrogen starvation with up-regulation of a novel glucosylglycerate hydrolase and depletion of the accumulated glucosylglycerate.

Authors:  Susana Alarico; Mafalda Costa; Marta S Sousa; Ana Maranha; Eva C Lourenço; Tiago Q Faria; M Rita Ventura; Nuno Empadinhas
Journal:  Sci Rep       Date:  2014-10-24       Impact factor: 4.379

9.  Octanoylation of early intermediates of mycobacterial methylglucose lipopolysaccharides.

Authors:  Ana Maranha; Patrick J Moynihan; Vanessa Miranda; Eva Correia Lourenço; Daniela Nunes-Costa; Joana S Fraga; Pedro José Barbosa Pereira; Sandra Macedo-Ribeiro; M Rita Ventura; Anthony J Clarke; Nuno Empadinhas
Journal:  Sci Rep       Date:  2015-09-01       Impact factor: 4.379
  9 in total

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