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Issue 30, 2015
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Chemical synthesis of the tumor-associated globo H antigen

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Abstract

A derivative of the tumor-associated globo H antigen, a complex hexasaccharide, was synthesized by a convergent and efficient [3 + 2 + 1] strategy using various glycosylation methods. All glycosylation reactions afforded good to excellent yields and outstanding stereoselectivity, including the installation of cis α-linked D-galactose and L-fucose. The longest linear sequence for this synthesis was 11 steps from a galactose derivative 11 to give an overall yield of 2.6%. The synthetic target had a free and reactive amino group at the glycan reducing end, facilitating its conjugation with other molecules for various applications.

Graphical abstract: Chemical synthesis of the tumor-associated globo H antigen

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Supplementary files

Article information


Submitted
13 Jan 2015
Accepted
24 Feb 2015
First published
24 Feb 2015

RSC Adv., 2015,5, 23311-23319
Article type
Paper
Author version available

Chemical synthesis of the tumor-associated globo H antigen

S. S. Mandal, G. Liao and Z. Guo, RSC Adv., 2015, 5, 23311
DOI: 10.1039/C5RA00759C

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