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• W4327698599 abstract "Naturally occurring peptides with high membrane permeability often have ester bonds on their backbones. However, the impact of amide-to-ester substitutions on the membrane permeability of peptides has not been directly evaluated. Here we report the effect of amide-to-ester substitutions on the membrane permeability and conformational ensemble of cyclic peptides related to membrane permeation. Amide-to-ester substitutions are shown to improve the membrane permeability of dipeptides and a model cyclic hexapeptide. NMR-based conformational analysis and enhanced sampling molecular dynamics simulations suggest that the conformational transition of the cyclic hexapeptide upon membrane permeation is differently influenced by an amide-to-ester substitution and an amide N-methylation. The effect of amide-to-ester substitution on membrane permeability of other cyclic hexapeptides, cyclic octapeptides, and a cyclic nonapeptide is also investigated to examine the scope of the substitution. Appropriate utilization of amide-to-ester substitution based on our results will facilitate the development of membrane-permeable peptides." @default.
• W4327698599 created "2023-03-18" @default.
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• W4327698599 date "2023-03-17" @default.
• W4327698599 modified "2023-10-14" @default.
• W4327698599 title "Amide-to-ester substitution as a stable alternative to N-methylation for increasing membrane permeability in cyclic peptides" @default.
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• W4327698599 doi "https://doi.org/10.1038/s41467-023-36978-z" @default.
• W4327698599 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/36932083" @default.
• W4327698599 hasPublicationYear "2023" @default.
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