Issue 45, 2015
From the journal:

Organic & Biomolecular Chemistry

Total syntheses of disulphated glycosphingolipid SB1a and the related monosulphated SM1a†

Haruka Hirose,a   Hideki Tamai,a   Chao Gao,b   Akihiro Imamura,*a   Hiromune Ando,ac   Hideharu Ishida,a   Ten Feizib  and  Makoto Kiso*ac  

* Corresponding authors

a Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan
E-mail: aimamura@gifu-u.ac.jp, kiso@gifu-u.ac.jp
Tel: +81-58-293-3453

b Glycosciences Laboratory, Department of Medicine, Imperial College London, Hammersmith Campus, Du Cane Road, London W12 0NN, UK

c Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501, Japan

Abstract

Total syntheses of two natural sulphoglycolipids, disulphated glycosphingolipid SB1a and the structurally related monosulphated SM1a, are described. They have common glycan sequences and ceramide moieties and are associated with human epithelial carcinomas. The syntheses featured efficient glycan assembly and the glucosyl ceramide cassette as a versatile building block. The binding of the synthetic sulphoglycolipids by the carcinoma-specific monoclonal antibody AE3 was investigated using carbohydrate microarray technology.

Graphical abstract: Total syntheses of disulphated glycosphingolipid SB1a and the related monosulphated SM1a

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Article information

DOI
https://doi.org/10.1039/C5OB01744K
Article type
Paper
Submitted
20 Aug 2015
Accepted
15 Sep 2015
First published
24 Sep 2015
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 11105-11117

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Total syntheses of disulphated glycosphingolipid SB1a and the related monosulphated SM1a

H. Hirose, H. Tamai, C. Gao, A. Imamura, H. Ando, H. Ishida, T. Feizi and M. Kiso, Org. Biomol. Chem., 2015, 13, 11105 DOI: 10.1039/C5OB01744K

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