Chemo-enzymatic synthesis of fluorinated sugar nucleotide: useful mechanistic probes for glycosyltransferases.
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.
Burkart
M D
MD
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, CA 92037, USA.
Vincent
S P
SP
Düffels
A
A
Murray
B W
BW
Ley
S V
SV
Wong
C H
CH
D000818:Animals; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D005643:Fucose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D005647:Fucosyltransferases / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D005700:Galactosyltransferases / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D012799:Sialyltransferases / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism
D003837:Deoxy Sugars; C418804:GDP-2F-fucose; C418802:GDP-6F-fucose; D009711:Nucleotides; C418788:UDP-2F-Gal; D005643:Fucose; D005647:Fucosyltransferases; D005700:Galactosyltransferases; D012799:Sialyltransferases