Exploration of the four-dimensional-conformational potential energy hypersurface of N-acetyl-L-aspartic acid N'-methylamide with its internally hydrogen bonded side-chain orientation

被引：11
|
作者：
Koo, JCP
Chass, GA
Perczel, A
Farkas, Ö
Torday, LL
Varro, A
Papp, JG
Csizmadia, IG [1 ]
机构：
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
[2] Velocet R & D, Toronto, ON M5G 2E8, Canada
[3] Eotvos Lorand Univ, Dept Organ Chem, H-1117 Budapest, Hungary
[4] Univ Szeged, Dept Pharmacol & Pharmacotherapy, H-6701 Szeged, Hungary
[5] Hungarian Acad Sci, Div Cardiovasc Pharmacol, H-6701 Szeged, Hungary
[6] Univ Szeged, H-6701 Szeged, Hungary
来源：
JOURNAL OF PHYSICAL CHEMISTRY A | 2002年 / 106卷 / 30期
关键词：
D O I：
10.1021/jp014514b
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Side-chain conformational potential energy hypersurfaces have been generated and analyzed for each of the nine possible backbone conformers of N-acetyl-L-aspartic acid-N' methylamide. A total of 37 out of the 81 possible conformers were found and optimized at the B3LYP/6-31G(d) level of theory. The relative energies as well as the stabilization exerted by the side-chain on the backbone have been calculated, at this level of theory, for the 37 optimized conformers. Various backbone-backbone (N-H...O=C) and backbone-side-chain (N-H...O=C; N-H...OH) hydrogen bonds were analyzed. The appearance of the notoriously absent alpha(L) backbone conformer was attributed to such a backbone-side-chain (BB-SC) hydrogen bonds as well as a very unusual backbone-backbone (BB-BB) hydrogen bond.
引用
收藏
页码：6999 / 7009
页数：11
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