Chemoenzymatic synthesis of the sialyl-alpha-(2-->3')-lactosamine trisaccharide with a 3-aminopropyl group as a spacer at the reducing end

Carbohydr Res. 2003 Jun 16;338(12):1265-70. doi: 10.1016/s0008-6215(03)00167-8.

Abstract

The trisaccharide, 3-aminopropyl 5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid-(2-->3)-beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranoside has been synthesized chemoenzymatically for the first time. First, the acceptor, 3-aminopropyl beta-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-beta-D-glucopyranoside was synthesized in a conventional chemical manner, and then it was coupled with CMP-sialic acid using alpha-(2-->3)-(N)-sialyltransferase to afford the desired trisaccharide by an enzymatically stereocontrolled manner.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Enzymes, Immobilized / chemistry
  • Enzymes, Immobilized / metabolism
  • Glucosides / chemical synthesis*
  • Glucosides / chemistry
  • Glycosylation
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Sialyltransferases / chemistry
  • Sialyltransferases / metabolism
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / chemistry

Substances

  • 3-aminopropyl-5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid-(2-3)-beta-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-beta-D-glucopyranoside
  • Enzymes, Immobilized
  • Glucosides
  • Oligosaccharides
  • Trisaccharides
  • sialooligosaccharides
  • Sialyltransferases