Construction of carbohydrate-based antitumor vaccines: synthesis of glycosyl amino acids by olefin cross-metathesis

Construction of carbohydrate-based antitumor vaccines: synthesis of glycosyl amino acids by olefin cross-metathesis
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DOI:
10.1016/s0040-4039(02)01336-9
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发表时间:
2002-08-26
影响因子:
1.8
通讯作者:
Danishefsky, SJ
Danishefsky, SJ
中科院分区:
化学4区
文献类型:
--
作者:
Biswas, K;Coltart, DM;Danishefsky, SJ

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The synthesis of biologically relevant glycosyl amino acids from corresponding O-allyl glycosides is described. The procedure involves a cross-meta thesis reaction with Fmoc-L-allylglycine benzyl ester, followed by reduction of the resulting olefin via catalytic hydrogenation, with the concomitant release of the free acid. This method has also been applied to the breast and prostate cancer antigen Globo-H, to afford a hexasaccharide glycosyl amino acid that has been previously incorporated in a polyvalent antitumor vaccine. (C) 2002 Published by Elsevier Science Ltd.