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Issue 7, 2006
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Synthesis of β-analogues of C-mannosyltryptophan, a novel C-glycosylamino acid found in proteins

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Abstract

α-C-Mannosyltryptophan (α-C-Man-Trp) has been found to be a novel post-translational modification of tryptophan found from some biologically important glycoproteins. In order to analyze the biological functions of α-C-Man-Trp, we have developed an efficient synthetic strategy for α-C-Man-Trp and its glucose and galactose analogues, starting from α-C-glycosidation of the corresponding hexapyranoside derivatives with tinacetylene. According to the synthetic routes, we describe here syntheses of β-anomers of C-Man-Trp, and its glucose and galactose analogues from the corresponding β-C-glycosylacetylenes. During this study, we have developed a highly stereocontrolled synthesis of β-C-mannosylacetylene that is required for the synthesis of β-C-Man-Trp, while the precedented method gave an anomeric mixture of the C-mannosylacetylene. The synthetic C-Man-Trp and its analogues were analyzed by HPLC.

Graphical abstract: Synthesis of β-analogues of C-mannosyltryptophan, a novel C-glycosylamino acid found in proteins

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Supplementary files

Article information


Submitted
16 Nov 2005
Accepted
27 Jan 2006
First published
16 Feb 2006

Org. Biomol. Chem., 2006,4, 1268-1277
Article type
Paper

Synthesis of β-analogues of C-mannosyltryptophan, a novel C-glycosylamino acid found in proteins

T. Nishikawa, Y. Koide, A. Kanakubo, H. Yoshimura and M. Isobe, Org. Biomol. Chem., 2006, 4, 1268
DOI: 10.1039/B516282C

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