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Structural Basis for Enantioselectivity in the Transfer Hydrogenation of a Ketone Catalyzed by an Artificial Metalloenzyme
Author(s) -
Cherrier Mickaël V.,
Engilberge Sylvain,
Amara Patricia,
Chevalley Alice,
Salmain Michèle,
FontecillaCamps Juan C.
Publication year - 2013
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201300592
Subject(s) - chemistry , ketone , transfer hydrogenation , catalysis , aryl , enantiomer , biocatalysis , enantiomeric excess , chiral resolution , stereochemistry , organic chemistry , enantioselective synthesis , reaction mechanism , ruthenium , alkyl
The crystal structure of bovine β‐lactoglobulin bound to a complex consisting of a (η 5 ‐Cp*)Rh(2,2′‐dipyridylamine) head and a lauric acid derived hydrophobic tail has been solved at 1.85 Å resolution. Previous work has shown that this hybrid catalyzes the transfer hydrogenation of an aryl ketone in neat water with formate as hydrogen donor with enantiomeric excess ( ee ) of about 26 %. Calculations using the X‐ray model indicate that the complex head can adopt discrete conformations, which may explain the ee observed.