Naslov
Synthesis and X-ray crystal structure study of the hydroxyurea and hydantoin derivatives of L-valine

Autori
Opačić, Ninoslav ; Zorc, Branka ; Cetina, Mario ; Mrvoš-Sermek, Draginja ; Raić-Malić, Silvana ; Mintas, Mladen

Izvornik
The journal of peptide research (1397-002X) 66 (2005), 2; 85-93

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

Ključne riječi
hydantoin ; hydrogen- bonding ; hydroxyurea ; L-valine ; single crystal X-ray analysis

Sažetak
The novel hydroxyurea 5 derivative of L-valine was prepared by aminolysis of N-(1-benzotriazolecarbonyl)-L-valine cyclohexanemethylamide 4 with hydroxylamine. The corresponding hydantoin derivative 6 was synthesized by base catalyzed cyclization of the amide 4. The exact stereostructure of hydantoin derivative 6 has been determined by X-ray crystal structure analysis. The chiral atom of the hydantoin ring in 6 has S configuration what is in agreement with its configuration in the starting L-valine. The molecules of 6 are joined into infinite chains by N-H-O intermolecular hydrogen bond. The infinite chains are additionally linked by two C-H -O hydrogen bonds, thus forming two-dimensional network. The hydantoin derivative of L-valine 6 and its L-leucine analoque LH have similar packing arrangements, so they are homostructural.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA