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-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 60 Sayı: 13
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.tetlet.2019.02.036
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.911-915
  • Anahtar Kelimeler: Chemoenzymatic synthesis, Oligosaccharides, glycosylation, Heparin, Heparan sulfate, OLIGOSACCHARIDES, SPECIFICITY, CLEAVAGE, DESIGN
  • Gazi Üniversitesi Adresli: Evet

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.