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Cupin Variants as Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes

preprint
submitted on 31.12.2019, 12:09 and posted on 31.12.2019, 21:16 by Nobutaka Fujieda, Miho Yuasa, Yosuke Nishikawa, Genji Kurisu, Shinobu Itoh, Haruna Ichihashi
Cupin superfamily proteins (TM1459) work as a macromolecular ligand framework with a double-stranded beta-barrel structure ligating to a Cu ion through histidine side chains. Variegating the first coordination sphere of TM1459 revealed that H52A and H54A/H58A mutants effectively catalyzed the diastereo- and enantio-selective Michael addition reaction of nitroalkanes to an α,β-unsaturated ketone. Moreover, in silico substrate docking signified C106N and F104W single-point mutations, which inverted the diastereoselectivity of H52A and further improved the stereoselectivity of H54A/H58A, respectively.

History

Email Address of Submitting Author

fujieda@biochem.osakafu-u.ac.jp

Institution

Osaka Prefecture University

Country

Japan

ORCID For Submitting Author

0000-0003-1045-6063

Declaration of Conflict of Interest

No conflict of interest.

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