title: Design and synthesis of active heparan sulfate-based probes.
abstract: A chemoenzymatic approach for synthesizing heparan sulfate oligosaccharides with a reactive diazoacetyl saccharide residue is reported. The resultant oligosaccharides were demonstrated to serve as specific inhibitors for heparan sulfate sulfotransferases, offering a new set of tools to probe the structural selectivity for heparan sulfate-binding proteins.
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA.|School of Pharmacy, Shanghai Jiaotong University, Shanghai, 200240, China.
authors.forename: Wen
authors.initials: W
authors.lastname: Zhou
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA.
authors.forename: Po-Hung
authors.initials: PH
authors.lastname: Hsieh
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA.
authors.forename: Yongmei
authors.initials: Y
authors.lastname: Xu
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA.
authors.forename: Timothy R
authors.initials: TR
authors.lastname: O'Leary
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
authors.forename: Xuefei
authors.initials: X
authors.lastname: Huang
authors.affiliation: Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA.
authors.forename: Jian
authors.initials: J
authors.lastname: Liu
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006497:Heparan Sulfate / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D015238:Sulfotransferases / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: D004791:Enzyme Inhibitors; D006497:Heparan Sulfate; D015335:Molecular Probes; D015238:Sulfotransferases; C021350:heparitin sulfotransferase