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
Main Authors: DalPozzo, Alma, Ni, Minghong, Muzi, Laura, Caporale, Andrea, de Castiglione, Roberto, Kaptein, Bernard, Broxterman, Quirinus B, Formaggio, Fernando
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Bromides - chemistry
Catalysis
Chemistry
Chromatography, High Pressure Liquid
Combinatorial Chemistry Techniques
Exact sciences and technology
Hydrocarbons, Brominated - chemistry
Molecular Structure
Organic chemistry
Peptides
Peptides - chemical synthesis
Preparations and properties
Spectroscopy, Fourier Transform Infrared
Stereoisomerism
Structure-Activity Relationship
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cited_by cdi_FETCH-LOGICAL-a379t-cfbfb697fb01fb74cc772056abd8d2e2bcf893144a3b60695f926a017a0514943
cites cdi_FETCH-LOGICAL-a379t-cfbfb697fb01fb74cc772056abd8d2e2bcf893144a3b60695f926a017a0514943
container_end_page 6375
container_issue 18
container_start_page 6372
container_title Journal of organic chemistry
container_volume 67
creator DalPozzo, Alma
Ni, Minghong
Muzi, Laura
Caporale, Andrea
de Castiglione, Roberto
Kaptein, Bernard
Broxterman, Quirinus B
Formaggio, Fernando
description 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.
doi_str_mv 10.1021/jo020280w
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Amino Acids - chemistry
Bromides - chemistry
Catalysis
Chemistry
Chromatography, High Pressure Liquid
Combinatorial Chemistry Techniques
Exact sciences and technology
Hydrocarbons, Brominated - chemistry
Molecular Structure
Organic chemistry
Peptides
Peptides - chemical synthesis
Preparations and properties
Spectroscopy, Fourier Transform Infrared
Stereoisomerism
Structure-Activity Relationship
title Amino Acid Bromides:  Their N-Protection and Use in the Synthesis of Peptides with Extremely Difficult Sequences
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