期刊
ACS OMEGA
卷 6, 期 32, 页码 20992-21004出版社
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.1c02559
关键词
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资金
- MINCIENCIAS: Fondo Nacional de Financiamiento para la Ciencia, la Tecnologia y la Innovacion Francisco Jose de Caldas [848]
- Universidad Industrial de Santander [VIE-UIS 8855, VIE-UIS 007-2020/2020000274]
- MINCIENCIAS [110271250586]
Enzyme-substrate interactions are crucial in enzymatic catalysis, and QTAIM calculations provide detailed information about these interactions. D187 and H224 act as electron density reservoirs in the reaction, while covalent hydrogen bonds play a more important role than noncovalent hydrogen bonds. Additionally, weak n -> pi* interactions were identified through QTAIM and NBO analysis.
Enzyme-substrate interactions play a crucial role in enzymatic catalysis. Quantum theory of atoms in molecules (QTAIM) calculations are extremely useful in computational studies of these interactions because they provide very detailed information about the strengths and types of molecular interactions. QTAIM also provides information about the intramolecular changes that occur in the catalytic reaction. Here, we analyze the enzyme-substrate interactions and the topological properties of the electron density in the enantioselective step of the acylation of (R,S)-propranolol, an aminoalcohol with therapeutic applications, catalyzed by Candida antarctica lipase B. Eight reaction paths (four for each enantiomer) are investigated and the energies, atomic charges, hydrogen bonds, and n -> pi* interactions of propranolol, the catalytic triad (composed of D187, H224, and S105), and the oxyanion hole are analyzed. It is found that D187 acts as an electron density reservoir for H224, and H224 acts as an electron density reservoir for the active site of the protein. It releases electron density when the tetrahedral intermediate is formed from the Michaelis complex and receives it when the enzyme-product complex is formed. Hydrogen bonds can be grouped into noncovalent and covalent hydrogen bonds. The latter are stronger and more important for the reaction than the former. We also found weak n -> pi* interactions, which are characterized by QTAIM and the natural bond orbital (NBO) analysis.
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