Synthesis of a Systematic 64-Membered Heparan Sulfate Tetrasaccharide Library

被引：0
作者：
Baryal, Kedar N.
Ramadan, Sherif
Su, Guowei
Huo, Changxin
Zhao, Yuetao
Liu, Jian
Hsieh-Wilson, Linda C.
Huang, Xuefei
机构：
[1] Department of Chemistry, Michigan State University, 578 S. Shaw Lane, East Lansing, 48824, MI
[2] Chemistry Department, Faculty of Science, Benha University, Qaliobiya, Benha
[3] Glycan Therapeutics, 617 Hutton Street, Raleigh, 27606, NC
[4] School of Life Sciences, Central South University, Hunan, Changsha
[5] Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, 27599, NC
[6] Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, 91125, CA
[7] Institute for Quantitative Health Science and Engineering, Michigan State University, East Lansing, 48824, MI
[8] Department of Biomedical Engineering, Michigan State University, East Lansing, 48824, MI
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 01期
关键词：
biological activity; carbohydrates; heparan sulfate; library synthesis; oligosaccharides;
D O I：
10.1002/anie.202380162
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Heparan sulfate (HS) has multifaceted biological activities. To date, no libraries of HS oligosaccharides bearing systematically varied sulfation structures are available owing to the challenges in synthesizing a large number of HS oligosaccharides. To overcome the obstacles and expedite the synthesis, a divergent approach was designed, where 64 HS tetrasaccharides covering all possible structures of 2-O-, 6-O- and N-sulfation with the glucosamine-glucuronic acid-glucosamine-iduronic acid backbone were successfully produced from a single strategically protected tetrasaccharide intermediate. This extensive library helped identify the structural requirements for HS sequences to have strong fibroblast growth factor-2 binding but a weak affinity for platelet factor-4. Such a strategy to separate out these two interactions could lead to new HS-based potential therapeutics without the dangerous adverse effect of heparin-induced thrombocytopenia. © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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页数：1
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