Lipidic
Mesophases as Novel Nanoreactor Scaffolds for Organocatalysts: Heterogeneously
Catalyzed Asymmetric Aldol Reactions in Confined Water
Version 2 2018-01-23, 19:04
Version 1 2018-01-19, 15:20
Posted on 2018-01-23 - 19:04
The
unique molecular architecture of lipidic cubic phases (LCPs) and their
cubosome dispersions comprise a well-defined, curved bilayer that
spans the entire three-dimensional (3-D) material space, encompassing
a network of two periodic, curved, and nonintersecting 3-D aqueous
channels. The ensuing large lipid/water interfacial area makes these
biomaterials an interesting matrix for the lateral immobilization
of organocatalysts to catalyze organic reactions in confined water.
Herein, we report for the first time the design, synthesis, assembly,
and characterization of catalytically active LCPs and cubosomes and
demonstrate their applicability as self-assembled, biomimetic, and
recyclable nanoreactor scaffolds. Small-angle X-ray scattering, cryo-transmission
electron microscopy, and dynamic light scattering were applied for
the characterization of the mesophases. These mesophases can be recycled
and enable efficient catalytic activity as well as modulation of the
diastereo- and enantioselectivity for the aldol reaction of several
benzaldehyde derivatives and cyclohexanone in water.
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Duss, Michael; Salvati Manni, Livia; Moser, Laurent; Handschin, Stephan; Mezzenga, Raffaele; Jessen, Henning J.; et al. (2018). Lipidic
Mesophases as Novel Nanoreactor Scaffolds for Organocatalysts: Heterogeneously
Catalyzed Asymmetric Aldol Reactions in Confined Water. ACS Publications. Collection. https://doi.org/10.1021/acsami.7b19740
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AUTHORS (7)
MD
Michael Duss
LS
Livia Salvati Manni
LM
Laurent Moser
SH
Stephan Handschin
RM
Raffaele Mezzenga
HJ
Henning J. Jessen
EL
Ehud M. Landau
KEYWORDS
nanoreactor scaffoldsenantioselectivityself-assembledNovel Nanoreactor ScaffoldsHeterogeneously Catalyzed Asymmetric Aldol Reactionsorganocatalystbiomaterialcatalyzenonintersecting 3- Dapplicabilitymesophaseimmobilizationlipidcyclohexanonesynthesischaracterizationmatrixbenzaldehyde derivativesSmall-angle X-rayassemblymodulationdiastereocryo-transmission electron microscopymaterial spacealdol reactioncatalyticallybilayerLipidic MesophaseslipidicLCPConfined WaterHereincubosome dispersionsbiomimeticOrganocatalyst