Enantioselective transfer hydrogenation of ketone catalysed by artificial metalloenzymes derived from bovine β-lactoglobulin.

Artificial metalloproteins resulting from the embedding of half-sandwich Ru(II)/Rh(III) fatty acid derivatives within β-lactoglobulin catalysed the asymmetric transfer hydrogenation of trifluoroacetophenone with modest to good conversions and fair ee's.

[1]  M. Dziedzicka-Wasylewska,et al.  Structural and thermodynamic studies of binding saturated fatty acids to bovine β-lactoglobulin. , 2012, International journal of biological macromolecules.

[2]  M. Zeller,et al.  Transfer Hydrogenation in Water via a Ruthenium Catalyst with OH Groups near the Metal Center on a bipy Scaffold , 2011 .

[3]  M. Dziedzicka-Wasylewska,et al.  Bovine beta-lactoglobulin complex with palmitic acid , 2011 .

[4]  Thomas R Ward,et al.  Merging the best of two worlds: artificial metalloenzymes for enantioselective catalysis. , 2011, Chemical communications.

[5]  A. Baiker,et al.  Multiple cycle reaction mechanism in the enantioselective hydrogenation of α,α,α-trifluoromethyl ketones , 2011 .

[6]  Paul C J Kamer,et al.  Bioinspired catalyst design and artificial metalloenzymes. , 2011, Chemistry.

[7]  G. Koten,et al.  Covalent anchoring of a racemization catalyst to CALB-beads: towards dual immobilization of DKR catalysts , 2011 .

[8]  Thomas R Ward,et al.  Artificial metalloenzymes based on the biotin-avidin technology: enantioselective catalysis and beyond. , 2011, Accounts of chemical research.

[9]  G. Jaouen,et al.  (Eta6-arene) ruthenium(II) complexes and metallo-papain hybrid as Lewis acid catalysts of Diels-Alder reaction in water. , 2010, Dalton transactions.

[10]  I. Arends,et al.  On the nature of mutual inactivation between [Cp*Rh(bpy)(H2O)]2+ and enzymes – analysis and potential remedies , 2010 .

[11]  Tillmann Heinisch,et al.  Design strategies for the creation of artificial metalloenzymes. , 2010, Current opinion in chemical biology.

[12]  L. Toupet,et al.  New dipyridylamine ruthenium complexes for transfer hydrogenation of ary ketones in water , 2010 .

[13]  Babulal Das,et al.  Study of half-sandwich platinum group metal complexes bearing dpt-NH2 ligand , 2010 .

[14]  R. Fish,et al.  Aqueous organometallic chemistry. 3. Catalytic hydride transfer reactions with ketones and aldehydes using [Cp*Rh(bpy)(H2O)](OTf)2 as the precatalyst and sodium formate as the hydride source: Kinetic and activation parameters, and the significance of steric and electronic effects , 2010 .

[15]  Yi Lu,et al.  Design of functional metalloproteins , 2009, Nature.

[16]  H. Dijkstra,et al.  Solid-state structural characterization of cutinase-ECE-pincer-metal hybrids. , 2009, Chemistry.

[17]  H. Sugihara,et al.  pH-Dependent catalytic activity and chemoselectivity in transfer hydrogenation catalyzed by iridium complex with 4,4'-dihydroxy-2,2'-bipyridine. , 2008, Chemistry.

[18]  T. Ward,et al.  Artificial metalloenzymes as selective catalysts in aqueous media , 2008 .

[19]  R. Stenkamp,et al.  X-ray structure and designed evolution of an artificial transfer hydrogenase. , 2008, Angewandte Chemie.

[20]  J. Canivet,et al.  Water-Soluble Phenanthroline Complexes of Rhodium, Iridium and Ruthenium for the Regeneration of NADH in the Enzymatic Reduction of Ketones , 2007 .

[21]  J. Canivet,et al.  Mono and dinuclear rhodium, iridium and ruthenium complexes containing chelating 2,2′-bipyrimidine ligands: Synthesis, molecular structure, electrochemistry and catalytic properties , 2007 .

[22]  Manfred T. Reetz,et al.  Directed evolution of enantioselective hybrid catalysts: a novel concept in asymmetric catalysis , 2007 .

[23]  Yi Lu Biosynthetic inorganic chemistry. , 2006, Angewandte Chemie.

[24]  Sylwester Mazurek,et al.  Artificial transfer hydrogenases based on the biotin-(strept)avidin technology: fine tuning the selectivity by saturation mutagenesis of the host protein. , 2006, Journal of the American Chemical Society.

[25]  A. Heck,et al.  Lipase active-site-directed anchoring of organometallics: metallopincer/protein hybrids. , 2005, Chemistry.

[26]  B. Feringa,et al.  Merging homogeneous catalysis with biocatalysis; papain as hydrogenation catalyst. , 2005, Chemical communications.

[27]  J. Canivet,et al.  Cationic arene ruthenium complexes containing chelating 1,10-phenanthroline ligands , 2005 .

[28]  Yi Lu,et al.  Design and engineering of metalloproteins containing unnatural amino acids or non-native metal-containing cofactors. , 2005, Current opinion in chemical biology.

[29]  T. Ward,et al.  Artificial metalloenzymes based on biotin-avidin technology for the enantioselective reduction of ketones by transfer hydrogenation. , 2005, Proceedings of the National Academy of Sciences of the United States of America.

[30]  R. Morris,et al.  Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes , 2004 .

[31]  Z. Bikádi,et al.  Probing protein binding sites by circular dichroism spectroscopy. , 2004, Current drug discovery technologies.

[32]  Lindsay Sawyer,et al.  Invited Review: β-Lactoglobulin: Binding Properties, Structure, and Function , 2004 .

[33]  H. Sugihara,et al.  Transfer hydrogenation of a variety of ketones catalyzed by rhodium complexes in aqueous solution and their application to asymmetric reduction using chiral Schiff base ligands , 2003 .

[34]  Manfred T. Reetz,et al.  Towards the directed evolution of hybrid catalysts , 2002 .

[35]  S. Ogo,et al.  pH-Dependent Transfer Hydrogenation of Ketones with HCOONa as a Hydrogen Donor Promoted by (η6-C6Me6)Ru Complexes , 2002 .

[36]  A. Chan,et al.  Catalytic hydrogenation of itaconic acid in a biotinylated Pyrphos–rhodium(I) system in a protein cavity , 1999 .

[37]  E N Baker,et al.  Structural basis of the Tanford transition of bovine beta-lactoglobulin. , 1998, Biochemistry.

[38]  R J Pearce,et al.  Characterization by ionization mass spectrometry of lactosyl beta-lactoglobulin conjugates formed during heat treatment of milk and whey and identification of one lactose-binding site. , 1997, Journal of dairy science.

[39]  E. Dufour,et al.  Probing the fatty acid binding site of β-lactoglobulins , 1993 .

[40]  M. Salmain,et al.  Aqueous phase transfer hydrogenation of aryl ketones catalysed by achiral ruthenium(II) and rhodium(III) complexes and their papain conjugates , 2013 .

[41]  Jianliang Xiao,et al.  Asymmetric Transfer Hydrogenation in Water with Platinum Group Metal Catalysts , 2010 .

[42]  George M. Whitesides,et al.  Conversion of a protein to a homogeneous asymmetric hydrogenation catalyst by site-specific modification with a diphosphinerhodium(I) moiety , 1978 .