Abstract
An effective procedure for the synthesis of 2-deoxy-2-fluoro-sugar nucleotides via Select fluor-mediated electrophilic fluorination of glycals with concurrent nucleophilic addition or chemo-enzymatic transformation has been developed, and the fluorinated sugar nucleotides have been used as probes for glycosyltransferases, including fucosyltransferase III, V, VI, and VII, and sialyl transferases. In general, these fluorinated sugar nucleotides act as competitive inhibitors versus sugar nucleotide substrates and form a tight complex with the glycosyltransferase.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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Deoxy Sugars / chemical synthesis*
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Deoxy Sugars / chemistry
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Deoxy Sugars / metabolism
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Deoxy Sugars / pharmacology
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Fucose / analogs & derivatives
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Fucose / chemical synthesis*
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Fucose / chemistry
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Fucose / metabolism
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Fucose / pharmacology
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Fucosyltransferases / antagonists & inhibitors*
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Fucosyltransferases / chemistry
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Fucosyltransferases / metabolism
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Galactosyltransferases / antagonists & inhibitors*
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Galactosyltransferases / chemistry
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Galactosyltransferases / metabolism
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Nucleotides / chemical synthesis*
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Nucleotides / chemistry
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Nucleotides / metabolism
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Nucleotides / pharmacology
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Sialyltransferases / antagonists & inhibitors*
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Sialyltransferases / chemistry
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Sialyltransferases / metabolism
Substances
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Deoxy Sugars
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GDP-2F-fucose
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GDP-6F-fucose
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Nucleotides
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UDP-2F-Gal
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Fucose
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Fucosyltransferases
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Galactosyltransferases
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Sialyltransferases