Artículo
Peptide model XXVIII: An exploratory ab initio and density functional study on the side-chain-backbone interaction in N-acetyl-L-cysteine-N-methylamide and N-formyl-L-cysteinamide in their γL-backbone conformations
Zamora, Miguel Angel; Baldoni, Hector Armando
; Rodriguez, Ana Maria; Enriz, Ricardo Daniel
; Sosa, Carlos P.; Perczel, András; Kucsman, Árpád; Farkas, Ödön; Deretey, Eugen; Vank, Judith C.; Csizmadia, Imre Gyula
Fecha de publicación:
01/07/2002
Editorial:
National Research Council Canada-NRC Research Press
Revista:
Canadian Journal of Chemistry
ISSN:
0008-4042
e-ISSN:
1480-3291
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
A conformational and electronic study on the energetically preferred conformations (γL) of N- and C-protected L-cysteine (P-CONH-CH(CH2SH)-CONH-Q, where P and Q may be H or Me) was carried out. After restraining the backbone (BB) conformation to its global minimum (γL or C7eq), all nine possible side-chain (SC) conformations were subjected to geometry optimization at the HF/3-21G and the B3LYP/6-31G(d,p) levels of theory. Seven of the nine side-chain conformers were located on the potential-energy surface. All conformers were subjected to an AIM (atoms in molecules) analysis. This study indicates that three of the seven optimized conformers exhibited either or both SC → BB- or BB → SC-type intramolecular hydrogen bonding. Five conformers, however, had distances between a proton and a heteroatom that suggested hydrogen bonding.
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Articulos(IMIBIO-SL)
Articulos de INST. MULTIDICIPLINARIO DE INV. BIO. DE SAN LUIS
Articulos de INST. MULTIDICIPLINARIO DE INV. BIO. DE SAN LUIS
Citación
Zamora, Miguel Angel; Baldoni, Hector Armando; Rodriguez, Ana Maria; Enriz, Ricardo Daniel; Sosa, Carlos P.; et al.; Peptide model XXVIII: An exploratory ab initio and density functional study on the side-chain-backbone interaction in N-acetyl-L-cysteine-N-methylamide and N-formyl-L-cysteinamide in their γL-backbone conformations; National Research Council Canada-NRC Research Press; Canadian Journal of Chemistry; 80; 7; 1-7-2002; 832-844
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