Syntheses of chondroitin sulfate tetrasaccharide structures containing 4,6-disulfate patterns and analysis of their interaction with glycosaminoglycan-binding protein

Bioorganic & Medicinal Chemistry Letters
Kento MiyachiYasuo Suda

Abstract

Chondroitin sulfate tetrasaccharide ligand conjugates, namely GlcA-GalNAc6S-GlcA-GalNAc4S6S (CS-C+E) 1, GlcA2S-GalNAc6S-GlcA2S-GalNAc4S6S (CS-D+T) 2, GlcA-GalNAc4S6S-GlcA-GalNAc4S (CS-E+A) 3, GlcA-GalNAc4S6S-GlcA-GalNAc6S (CS-E+C) 4, and GlcA-GalNAc4S6S-GlcA-GalNAc4S6S (CS-E+E) 5, were systematically synthesized using a disaccharide building block 6. Synthesized CS tetrasaccharide structures were immobilized onto gold-coated chips to prepare array-type sugar chips, and the binding properties of protein were evaluated by surface plasmon resonance imaging biosensor. CS-D+T, CS-E+A, CS-E+C, and CS-E+E showed greater affinity for basic fibroblast growth factor than did other tetrasaccharides (CS-C+D, C+E, D+D).

References

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Citations

Jun 18, 2017·Chemistry : a European Journal·Pedro Domínguez-RodríguezJavier Rojo
Jan 20, 2016·Chemistry : a European Journal·Cristina SoleraPedro M Nieto
Mar 2, 2019·Annual Review of Analytical Chemistry·Markéta BockováJiří Homola
Jul 16, 2019·Future Medicinal Chemistry·Shuang YangYinghong Wang
Jul 22, 2017·Angewandte Chemie·Jine LiJian Liu
Feb 13, 2019·Beilstein Journal of Organic Chemistry·Teresa Mena-BarragánPedro M Nieto
Aug 18, 2018·The Biochemical Journal·Anthony J Hayes, James Melrose
Jan 12, 2021·Frontiers in Cell and Developmental Biology·Wenshuang WangFuchuan Li
Oct 26, 2018·The Journal of Organic Chemistry·Wang YaoZhongjun Li
May 15, 2018·The Journal of Organic Chemistry·Shuang YangPingsheng Lei

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