Abstract
The pineal gland hormone melatonin regulates several physiological processes including circadian rhythm and also alleviates oxidative stress-induced degenerative diseases. In spite of its important biological roles, no high level ab initio conformational study has been conducted to reveal its structural features. In this work, the conformational flexibility of melatonin was investigated using correlated ab initio calculations. Conformers, obtained previously at the Hartree-Fock level (HF/6-31G*), were fully optimized using second order Møller-Plesset perturbation theory applying the frozen core approximation (MP2(FC)/6-31G*). Furthermore, single-point MP4(SDQ,FC)/6-31G*//MP2(FC)/6-31G* computations were performed to investigate the effect of higher order perturbation terms. The HF and MP2 conformational spaces are considerably different: the initial 128 structures converged into 102 different local minima as confirmed by frequency calculations; 28 new minima appeared and 26 previous HF local minima disappeared; no "all-trans" C3 side chain conformations are seen at the MP2(FC) level. The MP2 global minimum conformation is stabilized by an aromatic-side chain interaction.
| Original language | English |
|---|---|
| Pages (from-to) | 1466-1471 |
| Number of pages | 6 |
| Journal | Journal of Computational Chemistry |
| Volume | 29 |
| Issue number | 9 |
| DOIs | |
| State | Published - Jul 15 2008 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
- Safety, Risk, Reliability and Quality
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The effect of electron correlation on the conformational space of melatonin. / Csontos, József; Kálmán, Péter; Tasi, Gyula; Kálmán, Miklós; Murphy, Richard F.; Lovas, Sándor.
In: Journal of Computational Chemistry, Vol. 29, No. 9, 15.07.2008, p. 1466-1471.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - The effect of electron correlation on the conformational space of melatonin
AU - Csontos, József
AU - Kálmán, Péter
AU - Tasi, Gyula
AU - Kálmán, Miklós
AU - Murphy, Richard F.
AU - Lovas, Sándor
PY - 2008/7/15
Y1 - 2008/7/15
N2 - The pineal gland hormone melatonin regulates several physiological processes including circadian rhythm and also alleviates oxidative stress-induced degenerative diseases. In spite of its important biological roles, no high level ab initio conformational study has been conducted to reveal its structural features. In this work, the conformational flexibility of melatonin was investigated using correlated ab initio calculations. Conformers, obtained previously at the Hartree-Fock level (HF/6-31G*), were fully optimized using second order Møller-Plesset perturbation theory applying the frozen core approximation (MP2(FC)/6-31G*). Furthermore, single-point MP4(SDQ,FC)/6-31G*//MP2(FC)/6-31G* computations were performed to investigate the effect of higher order perturbation terms. The HF and MP2 conformational spaces are considerably different: the initial 128 structures converged into 102 different local minima as confirmed by frequency calculations; 28 new minima appeared and 26 previous HF local minima disappeared; no "all-trans" C3 side chain conformations are seen at the MP2(FC) level. The MP2 global minimum conformation is stabilized by an aromatic-side chain interaction.
AB - The pineal gland hormone melatonin regulates several physiological processes including circadian rhythm and also alleviates oxidative stress-induced degenerative diseases. In spite of its important biological roles, no high level ab initio conformational study has been conducted to reveal its structural features. In this work, the conformational flexibility of melatonin was investigated using correlated ab initio calculations. Conformers, obtained previously at the Hartree-Fock level (HF/6-31G*), were fully optimized using second order Møller-Plesset perturbation theory applying the frozen core approximation (MP2(FC)/6-31G*). Furthermore, single-point MP4(SDQ,FC)/6-31G*//MP2(FC)/6-31G* computations were performed to investigate the effect of higher order perturbation terms. The HF and MP2 conformational spaces are considerably different: the initial 128 structures converged into 102 different local minima as confirmed by frequency calculations; 28 new minima appeared and 26 previous HF local minima disappeared; no "all-trans" C3 side chain conformations are seen at the MP2(FC) level. The MP2 global minimum conformation is stabilized by an aromatic-side chain interaction.
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U2 - 10.1002/jcc.20907
DO - 10.1002/jcc.20907
M3 - Article
C2 - 18270961
AN - SCOPUS:44449177871
VL - 29
SP - 1466
EP - 1471
JO - Journal of Computational Chemistry
JF - Journal of Computational Chemistry
SN - 0192-8651
IS - 9
ER -