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Expedient Synthesis of a Library of Heparan Sulfate‐Like "Head-to-Tail" Linked Multimers for Structure and Activity Relationship Studies

Zhang, Jicheng and Liang, Li and Yang, Weizhun and Ramadan, Sherif and Baryal, Kedar and Huo, Chang-Xin and Bernard, Jamie J. and Liu, Jian and Hsieh-Wilson, Linda and Zhang, Fuming and Linhardt, Robert J. and Huang, Xuefei (2022) Expedient Synthesis of a Library of Heparan Sulfate‐Like "Head-to-Tail" Linked Multimers for Structure and Activity Relationship Studies. Angewandte Chemie International Edition, 61 (48). Art. No. e202209730. ISSN 1433-7851. doi:10.1002/anie.202209730.

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Heparan sulfate (HS) plays important roles in many biological processes. The inherent complexity of naturally existing HS has severely hindered the thorough understanding of their structure-activity relationship. To facilitate biological studies, a new strategy has been developed to synthesize a HS-like pseudo-hexasaccharide library, where HS disaccharides were linked in a “head-to-tail” fashion from the reducing end of a disaccharide module to the non-reducing end of a neighboring module. Combinatorial syntheses of 27 HS-like pseudo-hexasaccharides were achieved. This new class of compounds bound with fibroblast growth factor 2 (FGF-2) with similar structure-activity trends as HS oligosaccharides bearing native glycosyl linkages. The ease of synthesis and the ability to mirror natural HS activity trends suggest that the new head-to-tail linked pseudo-oligosaccharides could be an exciting tool to facilitate the understanding of HS biology.

Item Type:Article
Related URLs:
URLURL TypeDescription
Yang, Weizhun0000-0001-5522-4026
Ramadan, Sherif0000-0002-8639-4105
Baryal, Kedar0000-0003-1840-7485
Bernard, Jamie J.0000-0002-3800-2576
Liu, Jian0000-0001-8552-1400
Hsieh-Wilson, Linda0000-0001-5661-1714
Linhardt, Robert J.0000-0003-2219-5833
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 to X.H., J.L. and L.H.; S10OD028523 to F.Z. and R.L.), National Institute of Environmental Health Sciences (R01ES030695 to J.J.B.), the National Science Foundation (DMR-1933525 to F.Z., J.L. and R.L.), and Michigan State University for financial support of our work. We would like to thank Prof. Erika Lisabeth (Assay Development and Drug Discovery Core, MSU) for her expert help on SPR data processing.
Funding AgencyGrant Number
Michigan State UniversityUNSPECIFIED
Issue or Number:48
Record Number:CaltechAUTHORS:20221107-999291600.29
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:117756
Deposited By: Research Services Depository
Deposited On:18 Nov 2022 21:18
Last Modified:18 Nov 2022 23:52

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