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

摘要

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-OMICRON-(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 P-lactoside,whereas the 2'-and 4'-deoxy derivatives were less active.The other derivatives were inactive,as expected.