M. Cetina, Z. Džolić, D. Mrvoš-sermek
May 1, 2004
Citations
0
Influential Citations
6
Citations
Journal
The journal of peptide research : official journal of the American Peptide Society
Abstract
The novel purine and pyrimidine derivatives of 1-aminocyclopropane-1-carboxylic acid 1 and 2 were obtained by alkylation of 6-(N-pyrrolyl)purine and thymine with methyl 1-benzamido-2-chloromethylcyclopropanecarboxylate. X-ray crystal structure analysis shows that the cyclopropane rings in 1 and 2 posses Z-configuration. The cyclopropane ring atoms and attached atoms of the benzamido and methoxycarbonyl moiety of both molecules are disposed perpendicularly to each other. The carbonyl oxygen of the methoxycarbonyl moiety adopts in both compounds a synperiplanar conformation with respect to the midpoint of the distal bond of the cyclopropane ring. The torsion angles Phi and psi for the 1-aminocyclopropane-1-carboxylic acid residue in 1 and 2 correspond to a folded conformation, while the torsion angles omega define antiperiplanar conformation. Intermolecular hydrogen bonds connect the molecules of 1 into dimers. Each dimer is hydrogen-bonded with four ethanol molecules, thus forming discrete unit. On the contrary, intermolecular hydrogen bonds link the molecules of 2 generating three-dimensional network.