In situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl) carbonate and its utilization for difficult couplings in solid-phase peptide synthesis.
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.
Falb
E
E
Peptor Ltd, Kiryat Weizmann, Rehovot, Israel.
Yechezkel
T
T
Salitra
Y
Y
Gilon
C
C
D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002712:Chlorides / Q000138:chemical synthesis; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D010705:Phosgene / Q000031:analogs & derivatives* / Q000737:chemistry
D000596:Amino Acids; D002264:Carboxylic Acids; D002712:Chlorides; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010456:Peptides, Cyclic; D010705:Phosgene; C111044:bis(trichloromethyl) carbonate