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DOI: 10.1055/s-0040-1707238
One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams
This work was supported by JSPS KAKENHI Grant Number JP16K18855.
Publikationsverlauf
Received: 17. Juni 2020
Accepted after revision: 09. Juli 2020
Publikationsdatum:
17. August 2020 (online)

Abstract
α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam ring to form the corresponding open-chain 2,2,2-trifluoroethyl esters as reactive intermediates. The trifluoroethyl esters were more electrophilic compared with the corresponding methyl ester and thereby accelerated the aminolysis with various amino acids to form β-amino acid peptides with α,α-difluoromethylene unit.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707238.
- Supporting Information
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For ribosome engineering, see:
For examples of non-fluorinated β-amino acids, see:
For examples of fluorinated β-amino acids, see: