TY - JOUR
T1 - β-Pseudopeptide foldamers. the homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac)
AU - Luppi, Gianluigi
AU - Galeazzi, Roberta
AU - Garavelli, Marco
AU - Formaggio, Fernando
AU - Tomasini, Claudia
PY - 2004/8/7
Y1 - 2004/8/7
N2 - A total synthesis in solution and a conformational analysis of the homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac) to the tetramer level are described. As the D-Oxac building block contains both an oxazolidin-2-one and a β-amino acid group, it may represent a new type of conformationally constrained tool for the construction of β-pseudopeptide foldamers. A conformational investigation using NMR and an extensive, unconstrained analysis with a Monte Carlo search to the octamer level, both in water and in chloroform, showed that these homo-oligomers tend to fold in a regular helical structure in a competitive solvent, such as water. Since aqueous solutions are of major relevance for biological systems, these molecules are good candidates for application to these environments.
AB - A total synthesis in solution and a conformational analysis of the homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac) to the tetramer level are described. As the D-Oxac building block contains both an oxazolidin-2-one and a β-amino acid group, it may represent a new type of conformationally constrained tool for the construction of β-pseudopeptide foldamers. A conformational investigation using NMR and an extensive, unconstrained analysis with a Monte Carlo search to the octamer level, both in water and in chloroform, showed that these homo-oligomers tend to fold in a regular helical structure in a competitive solvent, such as water. Since aqueous solutions are of major relevance for biological systems, these molecules are good candidates for application to these environments.
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U2 - 10.1039/b405856a
DO - 10.1039/b405856a
M3 - Article
C2 - 15280953
AN - SCOPUS:4344703528
VL - 2
SP - 2181
EP - 2187
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 15
ER -