Macrophomate synthase: QM/MM simulations address the Diels-Alder versus Michael-Aldol reaction mechanism

Journal of the American Chemical Society

Volumn 127, Issue 10, 2005, Pages 3577-3588

  Guimarães, Cristiano Ruch Werneck ^a   Udier Blagović, Marina ^a   Jorgensen, William L ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLATION; CATALYSIS; CHEMICAL BONDS; DEHYDRATION; DERIVATIVES; FUNGI; QUANTUM THEORY;

DECARBOXYLATION; ENOLATES; MOLECULAR MECHANICS (MM); TRANSITION STATES (TS);

REACTION KINETICS;

MACROPHOMATE SYNTHASE; SYNTHETASE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; DIELS ALDER REACTION; MICHAEL ADDITION; MOLECULAR MECHANICS; MONTE CARLO METHOD; PHASE TRANSITION; QUANTUM MECHANICS; SIMULATION;

EID: 14944360652     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja043905b     Document Type: Article

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49. B3LYP/6-31+G(d) calculations were performed to study the reaction between 2-pyrone and the enolate of acetaldehyde. No Diels-Alder TS could be obtained using a larger basis set for this additional, simplified model. Initial configurations for the Diels-Alder TS were optimized to the Michael TS, with a single negative eigenvalue corresponding to the appropriate C-C bond-forming mechanism. The bicyclic intermediate for this model is no longer a stationary point at this level of calculation. Initial configurations for the bicyclic intermediate optimized to the Michael intermediate. The potential energy difference between the Michael TS and intermediate is 13.5 kcal/mol.
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