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

Alan R. Katritzky; Parul Angrish; Deniz Hür; Kazuyuki Suzuki

doi:10.1055/s-2005-861782

PAPER

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

Alan R. Katritzky*, Parul Angrish, Deniz Hür, Kazuyuki Suzuki
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
e-Mail: katritzky@chem.ufl.edu;

Abstract

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Abstract

Crystalline, chirally stable N-(Cbz- and Fmoc-α-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 α-amino acids 1a-f.

Key words

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

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