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Theoretical studies of sulbactam: Reactions after acylation
Author(s) -
Zhu Feng,
Li Rui,
Feng Dacheng,
He Maoxia,
Cai Zhengting
Publication year - 2007
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.21307
Subject(s) - chemistry , ring (chemistry) , thiazole , acylation , enamine , sulbactam , imine , computational chemistry , lactam , tetrahedral carbonyl addition compound , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , biochemistry , antibiotics , antibiotic resistance , imipenem , nucleophile
DFT methods were used on the model molecular to determine the mechanism of β‐lactamase inhibitor. The results show that the thiazole ring can be opened as well as β‐lactam ring. The thiazole ring‐open product can be formed via β‐lactam ring‐open product or tetrahedral intermediate directly. Those products, in imine or enamine form, can tautomerize via hydrogen migration. The sulforious form products may be transformed into sulfonyl ones. Water or hydroxyl group in residues on active site will help lower the activation energy of above reactions, and if structure permitted, they also effect the route selection of whole reaction system. © 2007 Wiley Periodicals, Inc. Int J Quantum Chem, 2007