Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 28, Pages 8705-8715Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201104023
Keywords
conformation analysis; helical structures; molecular dynamics; peptidomimetics; protein folding
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Funding
- MIUR
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A very efficient synthesis of orthogonally protected 1H-azepine-4-amino-4-carboxylic acid, abbreviated as Azn, a conformationally restricted analogue of ornithine, was realized. It was obtained on a gram scale in good overall yield in five steps, three of which did not require isolation of the intermediates, starting from the readily available 1-amino-4-oxo-cyclohexane-4-carboxylic acid. Both enantiomers were used for the preparation of pentapeptide models containing Ala, Aib, and Azn. Conformational studies using both spectroscopic techniques (NMR, CD) and molecular dynamics on model 5-mer peptides showed that the (R)-Azn isomer possesses a marked helicogenic effect.
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