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

Academic Article
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Overview

related to degree

  • Steensma, Ruo Wang, Ph.D. in Chemistry, Scripps Research 1990 - 1995

authors

  • Hayashi, T.
  • Murray, B. W.
  • Steensma, Ruo Wang
  • Wong, Chi-Huey

publication date

  • March 1997

journal

  • Bioorganic & Medicinal Chemistry  Journal

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.

subject areas

  • Enzyme Inhibitors
  • Kinetics
  • Models, Chemical
  • N-Acetyllactosamine Synthase
  • Uridine Diphosphate Galactose
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Identity

International Standard Serial Number (ISSN)

  • 0968-0896

Digital Object Identifier (DOI)

  • 10.1016/s0968-0896(96)00263-5

PubMed ID

  • 9113327
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Additional Document Info

start page

  • 497

end page

  • 500

volume

  • 5

issue

  • 3

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