Literature DB >> 16750179

Synthesis of the C1-phosphonate analog of UDP-GlcNAc.

Robert Chang1, Thanh-Trang Vo, Nathaniel S Finney.   

Abstract

We describe the first synthesis of the C1-phosphonate analog of UDP-GlcNAc, based on a new preparation of the corresponding glycosyl phosphonate. This C-glycosyl analog is shown to be a very weak inhibitor (Ki>10 mM) of fungal chitin synthase, indicating that at least in this case the replacement of the anomeric oxygen with a methylene group is not an innocent substitution.

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Year:  2006        PMID： 16750179     DOI： 10.1016/j.carres.2006.05.008

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


  6 in total

1.  A convenient synthesis of the C-1-phosphonate analogue of UDP-GlcNAc and its evaluation as an inhibitor of O-linked GlcNAc transferase (OGT).

Authors:  Jan Hajduch; Ghilsoo Nam; Eun Ju Kim; Roland Fröhlich; John A Hanover; Kenneth L Kirk
Journal:  Carbohydr Res       Date:  2007-11-01       Impact factor: 2.104

2.  Synthesis of uridine 5'-diphosphoiduronic acid: a potential substrate for the chemoenzymatic synthesis of heparin.

Authors:  Michel Weïwer; Trevor Sherwood; Dixy E Green; Miao Chen; Paul L DeAngelis; Jian Liu; Robert J Linhardt
Journal:  J Org Chem       Date:  2008-08-30       Impact factor: 4.354

3.  Substrate and product analogues as human O-GlcNAc transferase inhibitors.

Authors:  Helge C Dorfmueller; Vladimir S Borodkin; David E Blair; Shalini Pathak; Iva Navratilova; Daan M F van Aalten
Journal:  Amino Acids       Date:  2010-07-17       Impact factor: 3.520

4.  Synthesis of syn-gamma-amino-beta-hydroxyphosphonates by reduction of beta-ketophosphonates derived from L-proline and L-serine.

Authors:  Mario Ordóñez; Selene Lagunas-Rivera; Emanuel Hernández-Núñez; Victoria Labastida-Galván
Journal:  Molecules       Date:  2010-03-04       Impact factor: 4.411

5.  Structural insights into mechanism and specificity of O-GlcNAc transferase.

Authors:  Andrew J Clarke; Ramon Hurtado-Guerrero; Shalini Pathak; Alexander W Schüttelkopf; Vladimir Borodkin; Sharon M Shepherd; Adel F M Ibrahim; Daan M F van Aalten
Journal:  EMBO J       Date:  2008-09-25       Impact factor: 11.598

6.  Structural basis of the molecular ruler mechanism of a bacterial glycosyltransferase.

Authors:  Ana S Ramírez; Jérémy Boilevin; Ahmad Reza Mehdipour; Gerhard Hummer; Tamis Darbre; Jean-Louis Reymond; Kaspar P Locher
Journal:  Nat Commun       Date:  2018-01-31       Impact factor: 14.919
  6 in total

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