Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 51, Pages 16791-16795Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201811118
Keywords
cysteine; DOPA; enantioselectivity; molecular dynamics simulations; nanozymes
Categories
Funding
- NSFC [21431007, 21533008, 21820102009, 21871249]
- Key Program of Frontier of Sciences, CAS [QYZDJ-SSW-SLH052]
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Although various nanomaterials have been designed for biocatalysis, few of them can accelerate chemical reactions with high selectivity and stereocontrol, which remains them from being perfect alternatives to nature enzymes. Herein, inspired by the natural enzymes, an enantioselective nanomaterial has been constructed, with gold nanoparticles (AuNPs) as active centers, chiral cysteine (Cys) as selectors for chiral recognition, and expanded mesoporous silica (EMSN) as a skeleton of the artificial enzyme. In the oxidation of chiral 3,4-dihydroxy-phenylalanine (DOPA), the nanozyme with D-Cys shows preference to L-DOPA while the artificial enzyme with L-Cys shows preference to D-DOPA. Subsequent calculation of apparent steady-state kinetic parameters and activation energies together with molecular dynamics (MD) simulations showed that the different affinity precipitated by hydrogen bonding formation between chiral Cys and DOPA is the origin of chiral selectivity.
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