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Stochastic conformational search of brefeldin A and experimental structures
Author(s) -
Froimowitz Mark,
Gordon Douglas J.,
Moussa Adel,
Haidar Reem M.,
George Clifford
Publication year - 1999
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199911)12:11<858::aid-poc205>3.0.co;2-n
Subject(s) - conformational isomerism , ab initio , chemistry , brefeldin a , force field (fiction) , energy minimization , computational chemistry , molecule , ab initio quantum chemistry methods , stereochemistry , organic chemistry , physics , quantum mechanics , biochemistry , cell , golgi apparatus
The macrocyclic lactone brefeldin A was used as a test molecule for the MM3‐92 Stochastic Search conformational searching algorithm. A number of low energy conformers were found and 12 of these were also subjected to ab initio energy minimization using the 3–21 G * and 6–31 G * basis sets with the Spartan 5.0 package. There was reasonable agreement between the MM3‐92 and ab initio results in that almost all of the conformers found by the former were also stable low energy conformers with the latter. The structure of breflate, an ester analog of brefeldin, was also determined by X‐ray crystallography. There was very good agreement between experimental structures for the compound and the lowest energy conformer determined by the ab initio methods. This was also among the lowest conformers found by MM3‐92. Despite some imperfections in the MM3‐92 force field, the Stochastic Search method was a powerful method for determining molecular conformation. Copyright © 1999 John Wiley & Sons, Ltd.