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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. https://resolver.caltech.edu/CaltechAUTHORS:20230206-9587900.31

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Abstract

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
https://doi.org/10.1002/anie.202211985DOIArticle
ORCID:
AuthorORCID
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.
Funders:
Funding AgencyGrant Number
NIHR01GM072667
NIHU01GM116262
NIHR44GM134738
Michigan State UniversityUNSPECIFIED
Issue or Number:1
PubMed Central ID:PMC9933061
DOI:10.1002/anie.202211985
Record Number:CaltechAUTHORS:20230206-9587900.31
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20230206-9587900.31
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:119070
Collection:CaltechAUTHORS
Deposited By: Research Services Depository
Deposited On:09 Mar 2023 22:58
Last Modified:09 Mar 2023 22:58

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