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EnglishAn efficient synthesis of a 24 pseudopeptide membered ring in solution is reported in good yield. The cycle contains four units, all formed by an alpha-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 IR and 1H NMR spectroscopy and shows that the CHalpha hydrogens of the alpha-amino acids retain the very deshielded chemical shifts recorded in the spectra of the free precursors. Furthermore the NH hydrogens 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.
| Titolo: | Conformational Studies on a Medium Size Cyclopseudopeptide Containing the Oxazolidin-2-one Moiety |
| Autore/i: | ANGELICI, GAETANO; CASTELLUCCI, NICOLA; TOMASINI, CLAUDIA |
| Autore/i Unibo: | |
| Anno: | 2012 |
| Rivista: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/poc.2977 |
| Abstract: | 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 alpha-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 IR and 1H NMR spectroscopy and shows that the CHalpha hydrogens of the alpha-amino acids retain the very deshielded chemical shifts recorded in the spectra of the free precursors. Furthermore the NH hydrogens 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. |
| Data prodotto definitivo in UGOV: | 2013-05-30 17:51:50 |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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http://hdl.handle.net/11585/121547
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