Naslov
Crystal and molecular structure and conformational analysis of (1RS, 2SR)-1-[N-(tert-butoxycarbonyl)amino]-2-hydroxymethylcyclopropane-1-carboxylic acid

Autori
Cetina, Mario ; Hergold-Brundić, Antonija ; Raos, Nenad ; Žuža-Mak, Lora

Izvornik
Journal of molecular structure (0022-2860) 657 (2003), 1/3; 145-155

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
2 ; 3-methanoamino acids ; molecular mechanics ; global optimisation ; overlappling spheres method ; single crystal X-ray analysis

Sažetak
The crystal structure of (1RS, 2SR)-1-[N-(tert-butoxycarbonyl)amino]-2-hydroxymethylcyclopropane-1-carboxylic acid, a derivative of 1-aminocyclopropanecarboxylic acid (Acc), was determined by X-ray analysis. The molecule possesses the Z-configuration of the cyclopropane ring, a disordered carboxylic group, and a trans conformation of peptide bond. Intermolecular hydrogen bonds form R22(8) and R22(10) dimers and infinite chains along the b-axis. Mutually connected molecules are in ab-plane separated by hydrophobic channels formed between tert-butil groups and adjacent molecules. Conformational analysis using molecular-mechanics method, supported by the overlapping spheres method for finding the low-energy conformations, showed thet the conformation observed in crystal state had 2.8 kj mol-1 higher conformational energythan the lowest conformation. Calculations for the dimer consisting of x, y, z and x, y-1, z molecule showed a high correlation between the reproduction of crystal structure and similaritiy of its monomer units, which suggests that the symmetry of the dimer is not caused by crystal packing.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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