dc.contributor.author |
Coll, M.
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dc.contributor.author |
Frau Munar, Juan
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dc.contributor.author |
Donoso Pardo, Josefa Laurentina
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dc.contributor.author |
Muñoz Izquierdo, Francisco
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dc.date.accessioned |
2018-10-11T11:42:46Z |
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dc.identifier.uri |
http://hdl.handle.net/11201/148035 |
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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. |
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dc.format |
application/pdf |
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dc.relation.isformatof |
Versió postprint del document publicat a: https://doi.org/10.1016/S0166-1280(99)00250-X |
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dc.relation.ispartof |
Theochem-Journal of Molecular Structure, 1999, vol. 493, p. 287-299 |
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dc.subject.classification |
54 - Química |
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dc.subject.other |
54 - Chemistry. Crystallography. Mineralogy |
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dc.title |
PM3 study of reactivity of non-classical beta-lactam structures |
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dc.type |
info:eu-repo/semantics/article |
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dc.type |
info:eu-repo/semantics/acceptedVersion |
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dc.date.updated |
2018-10-11T11:42:46Z |
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dc.date.embargoEndDate |
info:eu-repo/date/embargoEnd/2075-01-01 |
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dc.embargo |
2075-01-01 |
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dc.rights.accessRights |
info:eu-repo/semantics/embargoedAccess |
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dc.identifier.doi |
https://doi.org/10.1016/S0166-1280(99)00250-X |
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