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Amino Acid Bromides:  Their N-Protection and Use in the Synthesis of Peptides with Extremely Difficult Sequences

Nα-Protected α-amino acid bromides were easily generated in situ with 1-bromo-N,N-2-trimethyl-1-propenylamine from the corresponding amino acids under very mild conditions. o-Nbs and the azido moieties proved to be compatible with these overactivated halides and were successfully applied in difficul...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-09, Vol.67 (18), p.6372-6375
Main Authors: DalPozzo, Alma, Ni, Minghong, Muzi, Laura, Caporale, Andrea, de Castiglione, Roberto, Kaptein, Bernard, Broxterman, Quirinus B, Formaggio, Fernando
Format: Article
Language:English
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Summary:Nα-Protected α-amino acid bromides were easily generated in situ with 1-bromo-N,N-2-trimethyl-1-propenylamine from the corresponding amino acids under very mild conditions. o-Nbs and the azido moieties proved to be compatible with these overactivated halides and were successfully applied in difficult peptide bond formations. N-Deprotection methods and the total step-by-step solution synthesis of a peptide containing up to seven consecutive l-(αMe)Valine residues are also reported. The assembly of this homopeptide was achieved in a short time and in very high yields by the azido/bromide system in a single repetitive operation.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo020280w