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Expanding the Chemical Diversity in Artificial Imine Reductases Based on the Biotin–Streptavidin Technology
Author(s) -
Quinto Tommaso,
Schwizer Fabian,
Zimbron Jeremy M.,
Morina Albert,
Köhler Valentin,
Ward Thomas R.
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201300825
Subject(s) - streptavidin , biotin , chemistry , imine , denticity , moiety , biotinylation , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , biochemistry , metal
Abstract We report on the optimization of an artificial imine reductase based on the biotin‐streptavidin technology. With the aim of rapidly generating chemical diversity, a novel strategy for the formation and evaluation of biotinylated complexes is disclosed. Tethering the biotin‐anchor to the Cp* moiety leaves three free coordination sites on a d 6 metal for the introduction of chemical diversity by coordination of a variety of ligands. To test the concept, 34 bidentate ligands were screened and a selection of the 6 best was tested in the presence of 21 streptavidin (Sav) isoforms for the asymmetric imine reduction by the resulting three legged piano stool complexes. Enantiopure α‐amino amides were identified as promising bidentate ligands: up to 63 % ee and 190 turnovers were obtained in the formation of 1‐phenyl‐1,2,3,4‐tetrahydroisoquinoline with [IrCp* biotin ( L ‐ThrNH 2 )Cl]⊂SavWT as a catalyst.