N-(Cbz- and Fmoc-α-aminoacyl)benzotriazoles:: Stable derivatives enabling peptide coupling of Tyr, Trp, Cys, Met, and Gln with free amino acids in aqueous media with complete retention of chirality

被引：54

作者：

Katritzky, AR ^{[1
]}

Angrish, P ^{[1
]}

Hür, D ^{[1
]}

Suzuki, K ^{[1
]}

机构：

[1] Univ Florida, Ctr Heterocycl Cpds, Dept Chem, Gainesville, FL 32611 USA

来源：

SYNTHESIS-STUTTGART | 2005年 / 03期

关键词：

N-(protected alpha-aminoacyl)benzotriazole; benzotriazole; amino acid; acylating reagent; peptide coupling;

D O I：

10.1055/s-2005-861782

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Crystalline, chirally stable N-(Cbz- and Fmoc-alpha-aminoacyl)benzotriazoles 2a-f, activated derivatives of Tyr, Trp, Cys, Met and Gln undergo peptide coupling in aqueous media with unprotected L-Ala-OH and L-Phe-OH to give the chiral dipeptides in 70-98% yield. A convenient and efficient procedure under mild reaction conditions for the preparation of 2a-f in 72-95% yield utilizes N-Cbz- or N-Fmoc-protected alpha-amino acids 1a-f.

引用

页码：397 / 402

页数：6

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