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Research article - Peer-reviewed, 2005

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

Westerlind U, Hagback P, Tidback B, Wiik L, Blixt O, Razi N, Norberg T

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

Authors' information

Westerlind, Ulrika
Swedish University of Agricultural Sciences, Department of Chemistry
Hagback, Per
Swedish University of Agricultural Sciences, Department of Chemistry
Norberg, Thomas
Swedish University of Agricultural Sciences, Department of Chemistry
Nahid, Razi
Tidbäck, Björn
Swedish University of Agricultural Sciences, Department of Chemistry
Wiik, Lotta
Swedish University of Agricultural Sciences, Department of Chemistry

Publication Identifiers

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

URI (permanent link to this page)

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