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- W2022204223 abstract "The N-terminal nonapeptide domain of the fungal nonribosomal peptide antibiotics cephaibol A and cephaibol C (AcPheAib4LeuIvaGly- Aib) is reported to adopt a right-handed helical conformation in the crystalline state. However, this conformation is at odds with the left-handed helicity observed in solution in related synthetic oligomers capped with Ac-L-PheAib4 fragments. We report the synthesis of four diastereoisomers of the cephaibol N-terminal nonapeptide, and show by NMR and CD spectroscopy that the peptide containing the chiral amino acids Phe and Leu in the naturally occurring relative configuration exists in solution as an interconverting mixture of helical screw-sense conformers. In contrast, the nonapeptide containing the unnatural relative configuration at Phe and Leu adopts a single, stable helical screw-sense, which is left handed when the N-terminal Phe residue is L and right-handed when the N-terminal Phe residue is D." @default.
- W2022204223 created "2016-06-24" @default.
- W2022204223 creator A5003688394 @default.
- W2022204223 creator A5044280583 @default.
- W2022204223 creator A5050736909 @default.
- W2022204223 creator A5079804629 @default.
- W2022204223 date "2013-10-09" @default.
- W2022204223 modified "2023-09-24" @default.
- W2022204223 title "The N-Terminal Nonapeptide of Cephaibols A and C: A Naturally Occurring Example of Mismatched Helical Screw-Sense Control" @default.
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- W2022204223 doi "https://doi.org/10.1002/chem.201302648" @default.
- W2022204223 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24123376" @default.
- W2022204223 hasPublicationYear "2013" @default.
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