Controlled Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides. Issue 19 (30th March 2018)

• Record Type: Journal Article
• Authors: Lu, Weigang; Zong, Chengli; Chopra, Pradeep; Pepi, Lauren E.; Xu, Yongmei; Amster, I. Jonathan; Liu, Jian; Boons, Geert‐Jan
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 19(2018)
• Page Start: 5340
• Page End: 5344
• Publication Date: 2018-03-30
• Subjects: enzymes -- epimers -- heparan -- oligosaccharides -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201800387
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A chemoenzymatic approach has been developed for the preparation of diverse libraries of heparan sulfate (HS) oligosaccharides. It employs chemically synthesized oligosaccharides having a chemical entity at a GlcN residue, which in unanticipated manners influences the site of modification by NST, C5‐Epi/2‐OST and 6‐OST1 /6‐OST3, thus resulting in oligosaccharides differing in N / O ‐sulfation and epimerization pattern. The enzymatic transformations defined fine substrate requirements of NST, C5‐Epi, 2‐OST, and 6‐OST. Abstract : Sugar patterns : Enzymatic modifications of three chemically synthesized hexasaccharides, with or without a 6‐ O ‐methyl ether on a GlcN residue, using NST, C5‐Epi/2‐OST, and 6‐OST1 /6‐OST3 gave, in an expeditious way, a library of 21 hexasaccharides that differ in N / O ‐sulfation and epimerization pattern. The enzymatic transformations defined fine substrate requirements of NST, C5‐Epi, 2‐OST, and 6‐OST. Epi=epimerase, NST= N ‐sulfotransferase, OST= O ‐sulfotransferase.