Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-alpha-D-glucosamine-O-methylglycoside acceptor

Zhang X., Dickinson D. M., Lin L., Suflita M., BAYTAŞ S., Linhardt R. J.

TETRAHEDRON LETTERS, vol.60, no.13, pp.911-915, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 60 Issue: 13
  • Publication Date: 2019
  • Doi Number: 10.1016/j.tetlet.2019.02.036
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.911-915
  • Keywords: Chemoenzymatic synthesis, Oligosaccharides, glycosylation, Heparin, Heparan sulfate, OLIGOSACCHARIDES, SPECIFICITY, CLEAVAGE, DESIGN
  • Gazi University Affiliated: Yes

Abstract

Heparan sulfate tetrasaccharide 2 was efficiently prepared in seven steps through chemoenzymatic synthesis. A monosaccharide 5, N-acetyl-alpha-D-glucosamine- O-methylglycoside (GlcNAc-OMe), was successfully used as an acceptor in a heparosan synthase (pmHS2)-catalyzed glycosylation reaction. This avoided the multi-step synthesis of a more complex disaccharide acceptor 3, greatly simplifying the route to tetrasaccharide target 2. This approach provides a critical tetrasaccharide intermediate for subsequent chemoenzymatic transformation to fondaparinux and its analogues. (C) 2019 Elsevier Ltd. All rights reserved.