Microbial Diversification Of Diels–alder Cycloadducts By Whole Cells Of Penicillium Brasilianum

dc.creatorDin Z.U.
dc.creatorFill T.P.
dc.creatorDonatoni M.C.
dc.creatordos Santos C.A.A.
dc.creatorBrocksom T.J.
dc.creatorRodrigues-Filho E.
dc.date2016
dc.date2017-08-17T19:15:20Z
dc.date2017-08-17T19:15:20Z
dc.date.accessioned2018-03-29T05:21:54Z
dc.date.available2018-03-29T05:21:54Z
dc.identifierMolecular Diversity. Springer International Publishing, v. 20, n. 4, p. 877 - 885, 2016.
dc.identifier1381-1991
dc.identifier10.1007/s11030-016-9680-0
dc.identifierhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-84976628910&doi=10.1007%2fs11030-016-9680-0&partnerID=40&md5=3ed4502968f6e95a3aba2c39812419d6
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/323732
dc.identifier2-s2.0-84976628910
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1357895
dc.descriptionFunctionalizations of cycloadducts are important steps for the use of Diels–Alder reactions in the construction of complex cyclic or polycyclic molecules from relatively simple starting materials. In the present work, we studied the ability of Penicillium brasilianum to perform microbial transformations of racemic Diels–Alder endo-cycloadducts. Thus, Diels–Alder products, obtained from reacting cyclopentadiene or 2,3-dimethylbutadiene with alkylated para-benzoquinones, were transformed by the resting cells of P. brasilianum producing new functionalized polycyclic compounds. These biotransformations yielded novel products of oxidation and ring closure, reduction of the C=C or C=O in α , β -unsaturated system, and allylic hydroxylations. The reduction products (conjugated double bond and carbonyl group) were also synthesized, and the enantioselectivity of both in vitro and in vivo processes was evaluated. In all cases, the microbiological transformations were enantioselective. In silico docking studies of the Diels–Alder cycloadducts with P. brasilianum oxidoreductase “old yellow enzymes” shed more light on these transformations. © 2016, Springer International Publishing Switzerland.
dc.description20
dc.description4
dc.description877
dc.description885
dc.languageEnglish
dc.publisherSpringer International Publishing
dc.relationMolecular Diversity
dc.rightsfechado
dc.sourceScopus
dc.subjectDiels–alder Cycloadducts
dc.subjectEnantioselective Biotransformation
dc.subjectOye
dc.subjectPenicillium Brasilianum
dc.titleMicrobial Diversification Of Diels–alder Cycloadducts By Whole Cells Of Penicillium Brasilianum
dc.typeArtículos de revistas


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