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- Title
Cupin Variants as a Macromolecular Ligand Library for Stereoselective Michael Addition of Nitroalkanes.
- Authors
Fujieda, Nobutaka; Ichihashi, Haruna; Yuasa, Miho; Nishikawa, Yosuke; Kurisu, Genji; Itoh, Shinobu
- Abstract
Cupin superfamily proteins (TM1459) work as a macromolecular ligand framework with a double‐stranded β‐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 enantioselective Michael addition reaction of nitroalkanes to an α,β‐unsaturated ketone. Moreover, calculated substrate docking signified C106N and F104W single‐point mutations, which inverted the diastereoselectivity of H52A and further improved the stereoselectivity of H54A/H58A, respectively.
- Subjects
HISTIDINE; NITROALKANES; MICHAEL reaction
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 20, p7791
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202000129