NDLI: Sugar nucleotide recognition by Klebsiella pneumoniae UDP-d-galactopyranose mutase: Fluorinated substrates, kinetics and equilibria

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Organic & Biomolecular Chemistry Vol - 7 Issue - 4

Organic & Biomolecular Chemistry Vol - 7 Issue - 3

Organic & Biomolecular Chemistry Vol -6

Organic & Biomolecular Chemistry Vol -5

Organic & Biomolecular Chemistry Vol -4

Organic & Biomolecular Chemistry Vol -3

Organic & Biomolecular Chemistry Vol -2

Sugar nucleotide recognition by Klebsiella pneumoniae UDP-d-galactopyranose mutase: Fluorinated substrates, kinetics and equilibria

Content Provider	Royal Society of Chemistry (RSC)
Author	Errey, James C. Fairhurst, Shirley A. Field, Robert A. Mann, Maretta C. McNeil, Michael R. Percy, Jonathan M. Whitfield, Chris Hill, Lionel Naismith, James H.
Copyright Year	2009
Abstract	A series of selectively fluorinated and other substituted UDP-D-galactose derivatives have been evaluated as substrates for Klebsiella pneumoniaeUDP-D-galactopyranose mutase. This enzyme, which catalyses the interconversion of the pyranose and furanose forms of galactose as its UDP adduct, is a prospective drug target for a variety of microbial infections. We show that none of the 2″-, 3″- or 6″-hydroxyl groups of UDP-D-galactopyranose are essential for substrate binding and turnover. However, steric factors appear to play an important role in limiting the range of substitutions that can be accommodated at C-2″ and C-6″ of the sugar nucleotide substrate. Attempts to invert the C-2″ stereochemistry from equatorial to axial, changing D-galacto- to D-talo-configuration, in an attempt to exploit the higher percentage of furanose at equilibrium in the talo-series, met with no turnover of substrate.
Starting Page	1009
Ending Page	1016
Page Count	8
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	7
Issue Number	5
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b815549f
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	UDP Hydroxy group Enzyme Pyranose Nucleotide Carbohydrate Catalysis Stereochemistry Galactose Uridine diphosphate Adduct Furanose
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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