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- W2326496687 endingPage "10153" @default.
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- W2326496687 abstract "The peptide coupling reactions allowing the incorporation of trifluoromethyl substituted oxazolidine-type pseudoprolines (CF3-ΨPro) into peptide chains have been studied. While standard protocols can be used for the peptide coupling reaction at the C-terminal position of the CF3-ΨPro, acid chloride activation has to be used for the peptide coupling reaction at the N-terminal position to overcome the decrease of nucleophilicity of the CF3-ΨPro. We demonstrate that the N-amidification of a diastereomeric mixture of CF3-ΨPro using Fmoc-protected amino acid chloride without base gave the corresponding dipeptides as a single diastereomer (6 examples). The ratio of the cis and trans amide bond conformers was determined by NMR study, highlighting the role of the Xaa side chains in the control of the peptide backbone conformation. Finally a tripeptide bearing a central CF3-ΨPro has been successfully synthesized." @default.
- W2326496687 created "2016-06-24" @default.
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- W2326496687 date "2013-09-26" @default.
- W2326496687 modified "2023-10-12" @default.
- W2326496687 title "Incorporation of CF<sub>3</sub>–Pseudoprolines into Peptides: A Methodological Study" @default.
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- W2326496687 doi "https://doi.org/10.1021/jo401494q" @default.
- W2326496687 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24032630" @default.
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