In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate and its utilization for difficult couplings in solid-phase peptide synthesis

Authors


  • To cite this article:

    Falb, E., Yechezkel, T., Salitra, Y. & Gilon, C. In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate and its utilization for difficult couplings in solid-phase peptide synthesis.

    J. Peptide Res., 1999, 53, 000–000


Chaim Gilon
Department of Organic Chemistry
The Hebrew University
Jerusalem 91904
Israel
Tel: 972-2-658-5276
Fax: 972-2-658-6763
E-mail:gilon@vms.huji.ac.il

Abstract

Abstract: This paper reports procedures for the straightforward in situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate (BTC) and their utilization for difficult couplings during solid-phase peptide synthesis. The BTC-mediated coupling of all Fmoc-protected proteinogenic amino acids to a large variety of N-alkylated amino acid-peptidyl-resin was studied. The majority of the couplings proceeded with quantitative conversion and without racemization. The utilization of BTC-mediated coupling for facile solid-phase synthesis of backbone cyclic peptides is presented.

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