title: Divergent heparin oligosaccharide synthesis with preinstalled sulfate esters.
abstract: Traditional chemical synthesis of heparin oligosaccharides first involves assembly of the full length oligosaccharide backbone followed by sulfation. Herein, we report an alternative strategy in which the O-sulfate was introduced onto glycosyl building blocks as a trichloroethyl ester prior to assembly of the full length oligosaccharide. This allowed divergent preparation of both sulfated and non-sulfated building blocks from common advanced intermediates. The O-sulfate esters were found to be stable during glycosylation as well as typical synthetic manipulations encountered during heparin oligosaccharide synthesis. Furthermore, the presence of sulfate esters in both glycosyl donors and acceptors did not adversely affect the glycosylation yields, which enabled us to assemble multiple heparin oligosaccharides with preinstalled 6-O-sulfates.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
authors.forename: Gopinath
authors.initials: G
authors.lastname: Tiruchinapally
authors.forename: Zhaojun
authors.initials: Z
authors.lastname: Yin
authors.forename: Mohammad
authors.initials: M
authors.lastname: El-Dakdouki
authors.forename: Zhen
authors.initials: Z
authors.lastname: Wang
authors.forename: Xuefei
authors.initials: X
authors.lastname: Huang
mesh_terms: D006493:Heparin / Q000138:chemical synthesis*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013463:Sulfuric Acid Esters / Q000737:chemistry*
chemical_list: D009844:Oligosaccharides; D013463:Sulfuric Acid Esters; D006493:Heparin