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. 2015 Dec 7;13(45):11105-17.
doi: 10.1039/c5ob01744k. Epub 2015 Sep 24.

Total syntheses of disulphated glycosphingolipid SB1a and the related monosulphated SM1a

Haruka Hirose  1 , Hideki Tamai, Chao Gao, Akihiro Imamura, Hiromune Ando, Hideharu Ishida, Ten Feizi, Makoto Kiso
Affiliations

Total syntheses of disulphated glycosphingolipid SB1a and the related monosulphated SM1a

Haruka Hirose et al. Org Biomol Chem. .

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.

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Figures

Fig. 1
Fig. 1
Structures of SM1a and SB1a.
Fig. 2
Fig. 2
Retrosynthetic analysis of the target compounds, SB1a and SM1a.
Fig. 3
Fig. 3
Microarray analyses of mAb AE3 with naturally occurring and chemically synthesized SM1a and synthetic SB1a. The results shown are binding intensities with duplicated spots of the three glycolipids printed at 5 fmol in the arrays with error bars representing half of the difference between the two values.
Scheme 1
Scheme 1
Synthesis of galactose derivatives 9 and 13.
Scheme 2
Scheme 2
Synthesis of disaccharide acceptor 16.
Scheme 3
Scheme 3
Synthesis of common trisaccharide donor 3.
Scheme 4
Scheme 4
Synthesis of GlcCer cassette 4 followed by the glycosylation with 3.
Scheme 5
Scheme 5
Sulphobnation followed by global deprotection toward SM1a.
Scheme 6
Scheme 6
Conversion of 24 into SB1a through sulphonation followed by deprotection.
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