573692-87-2Relevant articles and documents
Synthesis of non-natural glycosylamino acids containing tumor-associated carbohydrate antigens
Keding, Stacy J.,Endo, Atsushi,Danishefsky, Samuel J.
, p. 7023 - 7031 (2003)
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.
Hydroxynorleucine as a glycosyl acceptor is an efficient means for introducing amino acid functionality into complex carbohydrates
Keding, Stacy J.,Atsushi, Endo,Biswas, Kaustav,Zatorski, Andrzej,Coltart, Don M.,Danishefsky, Samuel J.
, p. 3413 - 3416 (2007/10/03)
A new approach to the synthesis of biologically relevant glycosyl amino acids using a non-natural amino acid as the glycosyl acceptor is described. The procedure involves a glycosylation reaction of a suitable carbohydrate donor with Fmoc-L-hydroxynorleucine benzyl ester. This reaction results in the direct incorporation of the amino acid moiety. The acceptor can be used for the preparation of α- or β-O-linked glycosides depending upon the nature of the glycosyl donor. This method has been applied in the synthesis of six different tumor-associated carbohydrate antigens.
