Peptide-Chain Elongation Using Unprotected Amino Acids in a Micro-Flow Reactor.
amides
anhydrides
flow chemistry
peptides
synthetic methods
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
27 Nov 2019
27 Nov 2019
Historique:
received:
02
08
2019
revised:
28
08
2019
pubmed:
31
8
2019
medline:
14
1
2020
entrez:
31
8
2019
Statut:
ppublish
Résumé
Conventional peptide synthesis requires a deprotection step after each amidation step, which decreases synthetic efficiency. Therefore, peptide synthesis using unprotected amino acids is considered an ideal approach. Here, we report peptide chain elongation using unprotected amino acids via a mixed carbonic anhydride. Micro-flow technology enabled rapid mixing of an organic layer containing a protected amino acid or dipeptide and an aqueous layer containing an unprotected amino acid or dipeptide to accelerate the desired amidation, and this approach successfully suppressed undesired racemization/epimerization (≤0.4 %). Various di-, tri-, and tetra-peptides were obtained in good to high yields. This is the first report on peptide chain elongation that proceeds without severe racemization from unprotected amino acids using inexpensive, nonexplosive, less wasteful, and less toxic reagents.
Identifiants
pubmed: 31468609
doi: 10.1002/chem.201903531
doi:
Substances chimiques
Amino Acids
0
Peptides
0
Carbon Dioxide
142M471B3J
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
15091-15097Subventions
Organisme : Japan Science and Technology Agency
ID : JPMJMI18G7
Organisme : Japan Society for the Promotion of Science
ID : ID No. 19J14624
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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