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Synthesis of a Systematic 64-Membered Heparan Sulfate Tetrasaccharide Library

Baryal, Kedar N. and Ramadan, Sherif and Su, Guowei and Huo, Changxin and Zhao, Yuetao and Liu, Jian and Hsieh-Wilson, Linda C. and Huang, Xuefei (2023) Synthesis of a Systematic 64-Membered Heparan Sulfate Tetrasaccharide Library. Angewandte Chemie International Edition, 62 (1). Art. No. e202211985. ISSN 1433-7851. PMCID PMC9933061. doi:10.1002/anie.202211985.

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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.

Item Type:Article
Related URLs:
URLURL TypeDescription
Baryal, Kedar N.0000-0003-1840-7485
Ramadan, Sherif0000-0002-8639-4105
Su, Guowei0000-0003-2668-9275
Zhao, Yuetao0000-0003-1655-1723
Liu, Jian0000-0001-8552-1400
Hsieh-Wilson, Linda C.0000-0001-5661-1714
Huang, Xuefei0000-0002-6468-5526
Additional Information:We are grateful for financial supports from the National Institute of General Medical Sciences, NIH (R01GM072667, U01GM116262, and R44GM134738) and Michigan State University for financial support of our work.
Funding AgencyGrant Number
Michigan State UniversityUNSPECIFIED
Issue or Number:1
PubMed Central ID:PMC9933061
Record Number:CaltechAUTHORS:20230206-9587900.31
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:119070
Deposited By: Research Services Depository
Deposited On:09 Mar 2023 22:58
Last Modified:09 Mar 2023 22:58

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