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

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 sid...

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Detalles Bibliográficos
Autores: 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
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2002
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/127108
Acceso en línea:http://hdl.handle.net/11336/127108
Access Level:acceso abierto
Palabra clave:L-CYSTEINE DIAMIDES
SIDE-CHAIN POTENTIAL-ENERGY SURFACE
AB INITIO AND DFT GEOMETRY OPTIMIZATION
AIM ANALYSIS
INTRAMOLECULAR HYDROGEN BONDING
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descripción
Sumario: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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