Conformational studies on a medium size cyclopseudopeptide containing the oxazolidin-2-one moiety

An efficient synthesis of a 24 pseudopeptide membered ring in solution is reported in good yield. The cycle contains four units, all formed by an α‐amino acid (Xaa) and a 4‐carboxy‐5‐methyl‐oxazolidin‐2‐one group (4‐carboxy‐5‐methyl‐oxazolidin‐2‐one = Oxd) in the same configuration ( l or d). In the...

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Bibliographic Details
Published in:Journal of physical organic chemistry 2012-11, Vol.25 (11), p.965-970
Main Authors: Angelici, Gaetano, Castellucci, Nicola, Tomasini, Claudia
Format: Article
Language:English
Subjects:
1H NMR spectroscopy
conformational analysis
cyclization
cyclopseudopeptide
medium size ring
peptide coupling
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Summary:An efficient synthesis of a 24 pseudopeptide membered ring in solution is reported in good yield. The cycle contains four units, all formed by an α‐amino acid (Xaa) and a 4‐carboxy‐5‐methyl‐oxazolidin‐2‐one group (4‐carboxy‐5‐methyl‐oxazolidin‐2‐one = Oxd) in the same configuration ( l or d). In the final sequence, the four ll or dd units are alternated so that, after cyclization, cyclo‐( l‐Xaa‐ l‐Oxd‐ d‐Xaa‐ d‐Oxd‐ l‐Xaa‐ l‐Oxd‐ d‐Xaa‐ d‐Oxd) is formed. The conformational analysis of this compound has been performed by means of infrared and 1 H NMR spectroscopy and shows that the CHα hydrogens of the α‐amino acids retain the very deshielded chemical shifts recorded in the spectra of the free precursors. Furthermore, the NH hydrogen have a weak tendency to form cross peaks, thus suggesting that the cycle lies in a large circle able to host small molecules, thus this compound is a promising candidate for drug delivery studies. Copyright © 2012 John Wiley & Sons, Ltd. An efficient synthesis of a 24 pseudopeptide membered ring in solution is reported in good yield. The cycle contains alternate four α‐amino acids and four Oxd (Oxd = oxazolidin‐2‐one) groups, two in the l form and two in the d form. The conformational analysis of this compound has been performed by means of infrared and 1 H NMR spectroscopy and shows that the cycle lies in a large circle able to host small molecules.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.2977