Literature DB >> 9113327

A chemoenzymatic synthesis of UDP-(2-deoxy-2-fluoro)-galactose and evaluation of its interaction with galactosyltransferase.

T Hayashi1, B W Murray, R Wang, C H Wong.   

Abstract

Uridine 5'-diphospho-(2-deoxy-2-fluoro)galactose (UDP-2FGal), prepared and characterized for the first time by a chemoenzymatic method, was found to be a competitive inhibitor of beta-1,4-galactosyltransferase with a Ki value of 149 microM. This study supports that the glycosyltransferase reaction mechanism proceeds through a glycosidic cleavage transition state with sp2 character developed at the anomeric center.

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Year:  1997        PMID: 9113327     DOI: 10.1016/s0968-0896(96)00263-5

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  5 in total

Review 1.  Substrate and donor specificity of glycosyl transferases.

Authors:  B Ernst; R Oehrlein
Journal:  Glycoconj J       Date:  1999-02       Impact factor: 2.916

2.  Global metabolic inhibitors of sialyl- and fucosyltransferases remodel the glycome.

Authors:  Cory D Rillahan; Aristotelis Antonopoulos; Craig T Lefort; Roberto Sonon; Parastoo Azadi; Klaus Ley; Anne Dell; Stuart M Haslam; James C Paulson
Journal:  Nat Chem Biol       Date:  2012-06-10       Impact factor: 15.040

3.  Efficient chemoenzymatic synthesis of novel galacto-N-biose derivatives and their sialylated forms.

Authors:  Lei Li; Yonghui Liu; Tiehai Li; Wenjun Wang; Zaikuan Yu; Cheng Ma; Jingyao Qu; Wei Zhao; Xi Chen; Peng G Wang
Journal:  Chem Commun (Camb)       Date:  2015-06-28       Impact factor: 6.222

4.  Glycosyltransferase mechanisms: impact of a 5-fluoro substituent in acceptor and donor substrates on catalysis.

Authors:  Matthew C T Hartman; Songmin Jiang; Jeffrey S Rush; Charles J Waechter; James K Coward
Journal:  Biochemistry       Date:  2007-09-21       Impact factor: 3.162

5.  Discovery of inhibitors of Leishmania β-1,2-mannosyltransferases using a click-chemistry-derived guanosine monophosphate library.

Authors:  Phillip van der Peet; Julie E Ralton; Malcolm J McConville; Spencer J Williams
Journal:  PLoS One       Date:  2012-02-29       Impact factor: 3.240

  5 in total

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