Efficient stereoselective synthesis of gamma-N-glycosyl asparagines by N-glycosylation of primary amide groups |
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Authors: | Tanaka Hiroshi Iwata Yuki Takahashi Daisuke Adachi Masaatsu Takahashi Takashi |
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Institution: | Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan. |
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Abstract: | The efficient and elegant synthesis of N-glycosides by N-glycosylation of asparagine-containing peptides is described. Glycosylation of primary amides with glycosyl N-phenyltrifluoroimidates in the presence of a catalytic amount of TMSOTf in nitromethane smoothly proceeded to provide the corresponding N-glycosyl amino acids in excellent yields. This coupling method was adaptable to the coupling of various glycosyl donors with amino acids and peptides. |
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