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Synthesis of non-natural glycosylamino acids containing tumor-associated carbohydrate antigens

✍ Scribed by Stacy J Keding; Atsushi Endo; Samuel J Danishefsky

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 265 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)00935-9

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✦ Synopsis

The synthesis of biologically relevant glycosylamino acids using a non-natural amino acid as the glycosyl acceptor is described. The glycosylation reaction of a monosaccharide tri-chloroacetimidate donor with Fmoc-L-hydroxynorleucine benzyl ester provided the a-Olinked product. Conversely, when the glycosylation reaction was carried out with a glycal epoxide donor, the b-O-linked product predominated. We have used these two complementary glycosylation reactions to synthesize five different glycosylamino acids, each containing the Tn, TF, STn, Lewis y or Globo-H tumor-associated carbohydrate antigens.

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