612844-52-7Relevant academic research and scientific papers
Synthesis of non-natural glycosylamino acids containing tumor-associated carbohydrate antigens
Keding, Stacy J.,Endo, Atsushi,Danishefsky, Samuel J.
, p. 7023 - 7031 (2007/10/03)
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 α-O-linked product. Conversely, when the glycosylation reaction was carried out with a glycal epoxide donor, the β-O-linked product predominated. We have used these two complementary glycosylation reactions to synthesize five different glycosylamino acids, each containing the Tn, TF, STn, Lewisy or Globo-H tumor-associated carbohydrate antigens.
