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

preprint
submitted on 31.12.2019 and posted on 31.12.2019 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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