Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase

Abstract

Derivatives of lactose with the galactose ring substituents replaced by deoxy or acylamino functions were prepared. The 2'-, 3'-. 4'- and 6'-deoxy, 3'-acetamido and 3'-benzamido derivatives of phenyl 4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranoside (phenyl P-lactoside) were synthesized from disaccharide or monosaccharide precursors. The derivatives were tested as substrates for the N-acetylglucosaminyltransferase from Neisseria meningitidis, which uses lactosyl derivatives as acceptors and UDP-GlcNAc as the donor in a beta-(1-->3) glycosylation reaction. The 6'-deoxy derivative was nearly threefold as active as phenyl beta-lactoside, whereas the 2'- and 4'-deoxy derivatives were less active. The other derivatives were inactive, as expected. (C) 2004 Elsevier Ltd. All rights reserved

Published in

Carbohydrate Research
2005, volume: 340, number: 2, pages: 221-233
Publisher: ELSEVIER SCI LTD

SLU Authors

• Westerlind, Ulrika

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

• Hagback, Per

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

• Norberg, Thomas

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

Publication identifier

• DOI: https://doi.org/10.1016/j.carres.2004.11.017

Permanent link to this page (URI)

https://res.slu.se/id/publ/8072