Literature DB >> 26399908

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

Haruka Hirose1, Hideki Tamai, Chao Gao, Akihiro Imamura, Hiromune Ando, Hideharu Ishida, Ten Feizi, Makoto Kiso.   

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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Year:  2015        PMID： 26399908      PMCID： PMC4920060          DOI： 10.1039/c5ob01744k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  32 in total

Review 1.  Chemistry and functional distribution of sulfoglycolipids.

Authors:  I Ishizuka
Journal:  Prog Lipid Res       Date:  1997-12       Impact factor: 16.195

2.  Synthesis of sialyl Le(x) ganglioside analogues sulfated at C-6 of either the galactose or N-acetylglucosamine residues, and at both of the galactose and N-acetylglucosamine residues: probes for clarifying the real carbohydrate ligand of L-selectin.

Authors:  S Komba; H Ishida; M Kiso; A Hasegawa
Journal:  Carbohydr Res       Date:  1996-05-14       Impact factor: 2.104

3.  Neoglycolipid-based oligosaccharide microarray system: preparation of NGLs and their noncovalent immobilization on nitrocellulose-coated glass slides for microarray analyses.

Authors:  Yan Liu; Robert A Childs; Angelina S Palma; Maria A Campanero-Rhodes; Mark S Stoll; Wengang Chai; Ten Feizi
Journal:  Methods Mol Biol       Date:  2012

4.  Cancer-associated expression of glycolipid sulfotransferase gene in human renal cell carcinoma cells.

Authors:  K Honke; M Tsuda; Y Hirahara; N Miyao; T Tsukamoto; M Satoh; Y Wada
Journal:  Cancer Res       Date:  1998-09-01       Impact factor: 12.701

5.  Monoclonal antibodies directed to a disulfated glycosphingolipid, SB1a (GgOse4Cer-II3IV3-bis-sulfate), associated with human hepatocellular carcinoma.

Authors:  N Hiraiwa; N Iida; I Ishizuka; S Itai; K Shigeta; R Kannagi; Y Fukuda; H Imura
Journal:  Cancer Res       Date:  1988-12-01       Impact factor: 12.701

6.  Ganglioside GQ1b: efficient total synthesis and the expansion to synthetic derivatives to elucidate its biological roles.

Authors:  Akihiro Imamura; Hiromune Ando; Hideharu Ishida; Makoto Kiso
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

7.  Isolation and structural characterization of a mono-sulfated isoglobotetraosylceramide, the first sulfoglycosphingolipid of the isoglobo-series, from rat kidney.

Authors:  K Tadano-Aritomi; T Kasama; S Handa; I Ishizuka
Journal:  Eur J Biochem       Date:  1992-10-01

8.  A novel mono-sulfated pentaglycosylceramide with the isoglobo-series core structure in rat kidney.

Authors:  K Tadano-Aritomi; M Okuda; I Ishizuka; H Kubo; P Ireland
Journal:  Carbohydr Res       Date:  1994-12-02       Impact factor: 2.104

9.  Isolation and characterization of the sulfated gangliotriaosylceramide from rat kidney.

Authors:  K Tadano; I Ishizuka
Journal:  J Biol Chem       Date:  1982-02-10       Impact factor: 5.157

10.  Ligands for the beta-glucan receptor, Dectin-1, assigned using "designer" microarrays of oligosaccharide probes (neoglycolipids) generated from glucan polysaccharides.

Authors:  Angelina S Palma; Ten Feizi; Yibing Zhang; Mark S Stoll; Alexander M Lawson; Esther Díaz-Rodríguez; María Asunción Campanero-Rhodes; Júlia Costa; Siamon Gordon; Gordon D Brown; Wengang Chai
Journal:  J Biol Chem       Date:  2005-12-21       Impact factor: 5.157
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  1 in total

1.  Pondering the Structural Factors that Affect 1,2-trans-Galactosylation: A Lesson Learnt from 3-O-β-Galactosylation of Galactosamine.

Authors:  Qingjiang Li; Zhongwu Guo
Journal:  J Carbohydr Chem       Date:  2017-12-12       Impact factor: 1.667
  1 in total

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