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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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Published in: | Journal of organic chemistry 2002-09, Vol.67 (18), p.6372-6375 |
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Main Authors: | , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo020280w |