An Approach to Synthesize Chondroitin Sulfate-E (CS-E) Oligosaccharide Precursors

The Journal of Organic Chemistry
Shuang YangPingsheng Lei

Abstract

An approach was developed to synthesize chondroitin sulfate-E (CS-E) oligosaccharides by adopting a postglycosylation-transformation strategy: different from all of the traditional approaches, the characteristic groups of CS-E were introduced following the assembly of the oligosaccharides. The adjusted strategy rendered an easy chain elongation strategy. All of the elongation steps generated high yields with excellent glycosylation outcomes. An orthogonally protected disaccharide was used as the building block to provide flexibility for the group transformation and derivatization at the N-2 position of the GalNAc residue and the O-1,5 positions of the GlcA residue, thereby providing ready access for the further examination of the structure-activity relationship (SAR) of CS-E molecules.

References

Oct 4, 1996·The Journal of Organic Chemistry·José M. LassalettaRichard R. Schmidt
Jun 24, 2004·Journal of the American Chemical Society·Sarah E TullyLinda C Hsieh-Wilson
Jun 15, 2006·Journal of the American Chemical Society·Sarah E TullyLinda C Hsieh-Wilson
Aug 1, 2006·Nature Chemical Biology·Cristal I GamaLinda C Hsieh-Wilson
Oct 14, 2006·Chemistry : a European Journal·Lijun Huang, Xuefei Huang
Feb 16, 2008·Journal of the American Chemical Society·Manish RawatLinda C Hsieh-Wilson
Sep 21, 2010·Antiviral Research·Daisuke KatoTakashi Suzuki
Jan 13, 2012·Bioorganic & Medicinal Chemistry Letters·Jun-ichi TamuraHiroshi Kitagawa
Mar 15, 2015·Bioorganic & Medicinal Chemistry Letters·Masahiro WakaoYasuo Suda
Jan 20, 2016·Chemistry : a European Journal·Cristina SoleraPedro M Nieto
Jan 20, 2017·Glycoconjugate Journal·L DjerbalJcf Kwok
Jun 18, 2017·Chemistry : a European Journal·Pedro Domínguez-RodríguezJavier Rojo

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Citations

Jul 16, 2019·Future Medicinal Chemistry·Shuang YangYinghong Wang
Feb 13, 2019·Beilstein Journal of Organic Chemistry·Teresa Mena-BarragánPedro M Nieto
May 29, 2021·Organic & Biomolecular Chemistry·Myriam Torres-RicoPedro M Nieto
Oct 26, 2018·The Journal of Organic Chemistry·Wang YaoZhongjun Li

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