Synthesis of non-natural glycosylamino acids containing tumor-associated carbohydrate antigens |
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Authors: | Stacy J KedingAtsushi Endo Samuel J Danishefsky |
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Institution: | a Laboratory for Bioorganic Chemistry, Memorial Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA b Department of Chemistry, Columbia University, New York, NY 10027, USA |
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Abstract: | 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. |
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Keywords: | hydroxynorleucine glycosylation carbohydrate antigen glycosylamino acid carbohydrate-based antitumor vaccines |
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