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PM3 study of reactivity of non-classical beta-lactam structures

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dc.contributor.author Coll, M.
dc.contributor.author Frau Munar, Juan
dc.contributor.author Donoso Pardo, Josefa Laurentina
dc.contributor.author Muñoz Izquierdo, Francisco
dc.date.accessioned 2018-10-11T11:42:46Z
dc.identifier.uri http://hdl.handle.net/11201/148035
dc.description.abstract [eng] Various mechanisms for the alkaline hydrolysis of aza-beta-lactam (na), oxo-beta-lactam (oa) and thio-beta-lactam compounds (sa) were analysed on the basis of PM3 calculations in order to identify potential differences with classical beta-lactam antibiotics. Changes in the tetrahedral intermediate were studied via the cleavage of not only the bond between atoms at 7 and 4 as in classical beta-lactam antibiotics but also of that between those at 7 and 6, which was previously put forward as a plausible pathway for the hydrolysis of these compounds. Cleavage of the 7<br>6 bond was found to be the energetically more favourable pathway in the three compounds studied, both in the gas phase and in solution. Opening of the b-lactam ring at the 7<br>6 bond yields especially stable carbamates, which suggests a potential inhibitory action in serine-b-lactamases. Based on the computations, those hydrolysis products where the five-membered ring is opened by cleavage of the C5<br>S1 bond are highly stable.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1016/S0166-1280(99)00250-X
dc.relation.ispartof Theochem-Journal of Molecular Structure, 1999, vol. 493, p. 287-299
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title PM3 study of reactivity of non-classical beta-lactam structures
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-10-11T11:42:46Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1016/S0166-1280(99)00250-X


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