Total syntheses of disulphated glycosphingolipid SB1a and the related monosulphated SM1a
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Published version
Author(s)
Type
Journal Article
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.
Date Issued
2015-09-24
Date Acceptance
2015-09-15
Citation
Organic and Biomolecular Chemistry, 2015, 13, pp.11105-11117
ISSN
1472-7781
Publisher
Royal Society of Chemistry
Start Page
11105
End Page
11117
Journal / Book Title
Organic and Biomolecular Chemistry
Volume
13
Copyright Statement
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
License URL
Sponsor
National Institutes of Health
Wellcome Trust
Grant Number
569179
108430/Z/15/Z
Subjects
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
1ST TOTAL-SYNTHESIS
HUMAN HEPATOCELLULAR-CARCINOMA
CERAMIDE CASSETTE APPROACH
LE(X) GANGLIOSIDE ANALOGS
REAL CARBOHYDRATE LIGAND
RAT-KIDNEY
SULFATED GLYCOSPHINGOLIPIDS
L-SELECTIN
MONOCLONAL-ANTIBODIES
ISOGLOBO-SERIES
Carcinoma
Ceramides
Glycosphingolipids
Humans
Microarray Analysis
Polysaccharides
Sulfur Compounds
0304 Medicinal And Biomolecular Chemistry
0305 Organic Chemistry
1115 Pharmacology And Pharmaceutical Sciences
Organic Chemistry
Publication Status
Published