Journal
ACS CATALYSIS
Volume 5, Issue 8, Pages 4708-4712Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.5b01046
Keywords
DNA; metalloenzyme; asymmetric catalysis; Diels-Alder reaction; Cu(II) ion; ligand freedom; enantiomeric preference
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Funding
- Japan Society for the Promotion of Science (JSPS)
- WPI program (iCeMS, Kyoto University)
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We report here DNA metalloenzymes that catalyzed the asymmetric Diels-Alder reactions with high conversion, excellent endo/exo selectivities, and enantioselectivities up to -97% ee. Their catalytic-pocket architectures were organized using a rational design strategy based on the Cu(II) ion, the composition of nucleobases, and the incorporation of flexible linkers. Without using the mirror image of B-DNA, DNA metalloenzymes afforded the opposite enantiomer of the Diels-Alder product compared with those obtained using a supramolecular Cu(II)-dmbpy/st-DNA catalyst system. Furthermore, we devised DNA metalloenzymes without the incorporation of an artificial binding ligand and successfully performed Diels-Alder carbon-carbon bond-forming reactions. This study provides a new perspective on the catalytic repertoire of nucleic acids in the realm of protein-dominated metalloenzymes.
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