Chiral organocatalysts based on lipopeptide micelles for aldol reactions in water

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dc.citation.issue2
dc.citation.volume19
dc.contributor.authorSoares, B. M.
dc.contributor.authorAguilar, A. M. [UNIFESP]
dc.contributor.authorSilva, E. R.[INIFESP]
dc.contributor.authorCoutinho-Neto, M. D.
dc.contributor.authorHamley, I. W.
dc.contributor.authorReza, M.
dc.contributor.authorRuokolainen, J.
dc.contributor.authorAlves, W. A.
dc.coverageCambridge
dc.date.accessioned2020-07-17T14:03:15Z
dc.date.available2020-07-17T14:03:15Z
dc.date.issued2017
dc.description.abstractA comprehensive study of the self-assembly in water of a lipopeptide consisting of a sequence of L-proline, L-arginine and L-tryptophan with a hydrocarbon chain has been performed. Fluorescence assays were used to determine the critical aggregation concentration. In situ small-angle X-ray scattering (SAXS) and molecular dynamics simulations showed the presence of spherical micelles with diameters around 6 nm. In agreement with these results, cryo-TEM images showed globular aggregates with diameters ranging from approximate to 4 nm up to approximate to 9 nm. Furthermore, the lipopeptide catalytic activity has been tested for the direct aldol reaction between cyclohexanone and p-nitrobenzaldehyde, and we have observed that the self-association of the organocatalyst played a critical role in the enhanced activity. Water affects the selectivity, and poor results are obtained under neat reaction conditions. The location of the catalytic groups at the lipopetide/ water solvent interface also endowed unusual selectivity in the catalyzed aldol reactions. Under optimized reaction conditions, high yields (up to >99%), good enantioselectivity (ee up to 85%) and high diastereoselectivity (ds up to 92 : 8) were obtained.en
dc.description.affiliationUniv Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210580 Santo Andre, Brazil
dc.description.affiliationUniv Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, Brazil
dc.description.affiliationUniv Fed Sao Paulo, Dept Biofis, BR-04023062 Sao Paulo, Brazil
dc.description.affiliationUniv Reading, Dept Chem, Reading RG6 6AD, Berks, England
dc.description.affiliationAalto Univ, Sch Sci, Dept Appl Phys, POB 15100, FI-00076 Helsinki, Finland
dc.description.affiliationUnifespUniv Fed Sao Paulo, Dept Biofis, BR-04023062 Sao Paulo, Brazil
dc.description.sourceWeb of Science
dc.description.sponsorshipFAPESP
dc.description.sponsorshipCNPq
dc.description.sponsorshipCAPES
dc.description.sponsorshipRoyal Society-Wolfson Research Merit Award
dc.description.sponsorshipEPSRC Platform Grant "Nanostructured Polymeric Materials for Healthcare''
dc.description.sponsorshipSynchrotron SOLEIL
dc.description.sponsorshipIDFAPESP: 2015/24018-1
dc.description.sponsorshipIDFAPESP: 08/57805-2
dc.description.sponsorshipIDFAPESP: 2013/12674-6
dc.description.sponsorshipIDCNPq: 302923/2015-2
dc.description.sponsorshipIDCNPq: 400239/2014-0
dc.description.sponsorshipIDCNPq: 573672/2008-3
dc.description.sponsorshipIDEPSRC Platform Grant "Nanostructured Polymeric Materials for Healthcare': EP/L020599/1
dc.description.sponsorshipIDSynchrotron SOLEIL: 20140919
dc.format.extent1181-1189
dc.identifierhttp://dx.doi.org/10.1039/c6cp08135e
dc.identifier.citationPhysical Chemistry Chemical Physics. Cambridge, v. 19, n. 2, p. 1181-1189, 2017.
dc.identifier.doi10.1039/c6cp08135e
dc.identifier.issn1463-9076
dc.identifier.urihttps://repositorio.unifesp.br/handle/11600/55253
dc.identifier.wosWOS:000392399400027
dc.language.isoeng
dc.publisherRoyal Soc Chemistry
dc.relation.ispartofPhysical Chemistry Chemical Physics
dc.rightsinfo:eu-repo/semantics/restrictedAccess
dc.titleChiral organocatalysts based on lipopeptide micelles for aldol reactions in wateren
dc.typeinfo:eu-repo/semantics/article
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