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Synlett 2004(10): 1784-1788  
DOI: 10.1055/s-2004-829563
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Internally Fluorescence-Quenched Sugar Nucleotides

Frank Schweizer*a,b, Ole Hindsgaul*a, Monica M. Palcica
a Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada
b Department of Chemistry, University of Manitoba, Winnipeg, Manitoba R3T 2N2, Canada
Fax: +1(204)4747608; e-Mail: schweize@ms.umanitoba.ca; e-Mail: hindsgaul@crc.dk;
Further Information

Publication History

Received 7 April 2004
Publication Date:
15 July 2004 (online)

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Abstract

The synthesis of intramolecularly quenched UDP-Gal analogues bearing a fluorescence emitter attached to the galactose moiety and a quencher on the uracil portion is described. The rate of transfer using several galactosyltransferases was examined. Our results demonstrate that galactose-modified, sugar-nucleotide-modified and double modified UDP-Gal analogues are recognized as weak substrates by three of the galactosyltransferases.

Key words

carbohydrates - nucleotides - glycosylations - enzymes - oligosaccharides

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