In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate and its utilization for difficult couplings in solid-phase peptide synthesis |
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Authors: | E. Falb T. Yechezkel Y. Salitra C. Gion |
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Affiliation: | E. Falb,T. Yechezkel,Y. Salitra,C. Gi1on |
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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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Keywords: | acid chlorides backbone cyclic peptides bis-(trichloromethyl)carbonate difficult couplings N-alkylated amino acids solid-phase peptide synthesis |
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