In situ generation of Fmoc‐amino acid chlorides using bis‐(trichloromethyl)carbonate and its utilization for difficult couplings in solid‐phase peptide synthesis
- 1 May 1999
- journal article
- Published by Wiley in Chemical Biology & Drug Design
- Vol. 53 (5) , 507-517
- https://doi.org/10.1034/j.1399-3011.1999.00049.x
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.Keywords
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