Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups

Hiroshi Tanaka; Yuki Iwata; Daisuke Takahashi; Masaatsu Adachi; Takashi Takahashi

doi:10.1021/ja0450298

Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups

Hiroshi Tanaka, Yuki Iwata, Daisuke Takahashi, Masaatsu Adachi, Takashi Takahashi

Research output: Contribution to journal › Article › peer-review

73 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1630-1631
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	6
DOIs	https://doi.org/10.1021/ja0450298
Publication status	Published - 2005 Feb 16
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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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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AU - Tanaka, Hiroshi

AU - Iwata, Yuki

AU - Takahashi, Daisuke

AU - Adachi, Masaatsu

AU - Takahashi, Takashi

PY - 2005/2/16

Y1 - 2005/2/16

N2 - 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.

AB - 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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Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups

Abstract

ASJC Scopus subject areas

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