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, cilt.60, sa.13, ss.911-915, 2019 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 60 Konu: 13
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.tetlet.2019.02.036
  • Dergi Adı: TETRAHEDRON LETTERS
  • Sayfa Sayıları: ss.911-915

Özet

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.