27 publications

27 publications

Achiral Cyclopentadienone Iron Tricarbonyl Complexes Embedded in Streptavidin: An Access to Artificial Iron Hydrogenases and Application in Asymmetric Hydrogenation

Renaud, J.-L.; Ward, T. R.

Catal. Lett., 2016, 10.1007/s10562-015-1681-6

We report on the synthesis of biotinylated (cyclopentadienone)iron tricarbonyl complexes, the in situ generation of the corresponding streptavidin conjugates and their application in asymmetric hydrogenation of imines and ketones.


Metal: Fe
Ligand type: CO; Cyclopentadienone
Host protein: Streptavidin (Sav)
Anchoring strategy: Supramolecular
Optimization: Chemical
Reaction: Hydrogenation
Max TON: 20
ee: 34
PDB: ---
Notes: ---

An asymmetric catalyst

Akabori, S.; Sakurai, S.

Nature, 1956, 10.1038/178323b0

Asymmetric synthesis has hitherto succeeded only by using reagents or solvents having the asymmetric configuration.


Metal: Pd
Ligand type: Undefined
Host protein: Silk fibroin fibre
Anchoring strategy: Undefined
Optimization: ---
Reaction: Hydrogenation
Max TON: >22
ee: ---
PDB: ---
Notes: ---

Aqueous Phase Transfer Hydrogenation of Aryl Ketones Catalysed by Achiral Ruthenium(II) and Rhodium(III) Complexes and their Papain Conjugates

Salmain, M.

Appl. Organomet. Chem., 2013, 10.1002/aoc.2929


Metal: Rh
Ligand type: Cp*; Poly-pyridine
Host protein: Papain (PAP)
Anchoring strategy: Covalent
Optimization: Chemical
Reaction: Hydrogenation
Max TON: 96
ee: 15
PDB: ---
Notes: ---

Artificial Metalloenzymes Derived from Bovine β-Lactoglobulin for the Asymmetric Transfer Hydrogenation of an Aryl Ketone – Synthesis, Characterization and Catalytic Activity

Salmain, M.

Dalton Trans., 2014, 10.1039/c3dt53253d


Metal: Rh
Ligand type: Cp*; Poly-pyridine
Host protein: ß-lactoglobulin
Anchoring strategy: Supramolecular
Optimization: Chemical
Reaction: Hydrogenation
Max TON: 14
ee: 32
PDB: ---
Notes: ---

Artificial Metalloenzymes for Enantioselective Catalysis Based on Biotin-Avidin

Ward, T. R.

J. Am. Chem. Soc., 2003, 10.1021/ja035545i


Metal: Rh
Ligand type: Phosphine
Host protein: Streptavidin (Sav)
Anchoring strategy: Supramolecular
Optimization: Chemical & genetic
Reaction: Hydrogenation
Max TON: ---
ee: 96
PDB: ---
Notes: ---

Artificial Metalloenzymes for Enantioselective Catalysis: The Phenomenon of Protein Accelerated Catalysis

Ward, T. R.

J. Organomet. Chem., 2004, 10.1016/j.jorganchem.2004.09.032


Metal: Rh
Host protein: Streptavidin (Sav)
Anchoring strategy: Supramolecular
Optimization: Chemical
Reaction: Hydrogenation
Max TON: ---
ee: 94
PDB: ---
Notes: Reduction of acetamidoacrylic acid. 3.0-fold protein acceleration.

Metal: Rh
Host protein: Avidin (Av)
Anchoring strategy: Supramolecular
Optimization: Chemical
Reaction: Hydrogenation
Max TON: ---
ee: 39
PDB: ---
Notes: Reduction of acetamidoacrylic acid. 12.0-fold protein acceleration.

Artificial Metalloenzymes: (Strept)avidin as Host for Enantioselective Hydrogenation by Achiral Biotinylated Rhodium-Diphosphine Complexes

Ward, T. R.

J. Am. Chem. Soc., 2004, 10.1021/ja0476718


Metal: Rh
Ligand type: Phosphine
Host protein: Streptavidin (Sav)
Anchoring strategy: Supramolecular
Optimization: Chemical & genetic
Reaction: Hydrogenation
Max TON: ---
ee: 94
PDB: ---
Notes: ---

Asymmetric Hydrogenation with Antibody-Achiral Rhodium Complex

Harada, A.

Org. Biomol. Chem., 2006, 10.1039/B609242J


Metal: Rh
Ligand type: COD; Phosphine
Host protein: Antibody 1G8
Anchoring strategy: Antibody
Optimization: ---
Reaction: Hydrogenation
Max TON: ---
ee: ---
PDB: ---
Notes: ---

Burkavidin: A Novel Secreted Biotin-Binding Protein from the Human Pathogen Burkholderia Pseudomallei

Creus, M.

Protein Expression Purif., 2011, 10.1016/j.pep.2011.01.003


Metal: Rh
Ligand type: Diphenylphosphine
Host protein: Burkavidin
Anchoring strategy: Supramolecular
Optimization: Chemical & genetic
Reaction: Hydrogenation
Max TON: ~110
ee: 65
PDB: ---
Notes: ---

Catalytic Hydrogenation of Itaconic Acid in a Biotinylated Pyrphos-Rhodium(I) System in a Protein Cavity

Chan, A. S. C.

Tetrahedron: Asymmetry, 1999, 10.1016/S0957-4166(99)00193-7


Metal: Rh
Ligand type: Phosphine
Host protein: Avidin (Av)
Anchoring strategy: Supramolecular
Optimization: ---
Reaction: Hydrogenation
Max TON: 31
ee: 48
PDB: ---
Notes: ---

Chemically Engineered Papain as Artificial Formate Dehydrogenase for NAD(P)H Regeneration

Salmain, M.

Org. Biomol. Chem., 2011, 10.1039/c1ob05482a


Metal: Rh
Ligand type: Cp*; Poly-pyridine
Host protein: Papain (PAP)
Anchoring strategy: Covalent
Optimization: Chemical
Reaction: Hydrogenation
Max TON: ---
ee: ---
PDB: ---
Notes: TOF = 52.1 h-1 for NAD+

Chemical Optimization of Artificial Metalloenzymes Based on the Biotin-Avidin Technology: (S)-Selective and Solvent-Tolerant Hydrogenation Catalysts via the Introduction of Chiral Amino Acid Spacers

Ward, T. R.

Chem. Commun., 2005, 10.1039/b509015f


Metal: Rh
Ligand type: Phosphine
Host protein: Streptavidin (Sav)
Anchoring strategy: Supramolecular
Optimization: Chemical
Reaction: Hydrogenation
Max TON: ---
ee: ---
PDB: ---
Notes: ---

Conversion of a Protein to a Homogeneous Asymmetric Hydrogenation Catalyst by Site-Specific Modification with a Diphosphinerhodium (I) Moiety

Whitesides, G. M.

J. Am. Chem. Soc., 1978, 10.1021/ja00469a064


Metal: Rh
Ligand type: Phosphine
Host protein: Avidin (Av)
Anchoring strategy: Supramolecular
Optimization: ---
Reaction: Hydrogenation
Max TON: 500
ee: 41
PDB: ---
Notes: ---

Counter Propagation Artificial Neural Networks Modeling of an Enantioselectivity of Artificial Metalloenzymes

Novič, M.

Mol. Divers., 2007, 10.1007/s11030-008-9068-x


Metal: Rh
Ligand type: Diphenylphosphine
Host protein: Streptavidin (Sav)
Anchoring strategy: Supramolecular
Optimization: Chemical & genetic
Reaction: Hydrogenation
Max TON: ---
ee: 94
PDB: ---
Notes: Computational prediction of the enantioselectivity of the hydrogenation reaction catalysed by the ArM.

Directed Evolution of Hybrid Enzymes: Evolving Enantioselectivity of an Achiral Rh-Complex Anchored to a Protein

Reetz, M. T.

Chem. Commun., 2006, 10.1039/b610461d


Metal: Rh
Ligand type: COD; Phosphine
Host protein: Streptavidin (Sav)
Anchoring strategy: Supramolecular
Optimization: Genetic
Reaction: Hydrogenation
Max TON: 4500
ee: 65
PDB: ---
Notes: ---

Direct Hydrogenation of Carbon Dioxide by an Artificial Reductase Obtained by Substituting Rhodium for Zinc in the Carbonic Anhydrase Catalytic Center. A Mechanistic Study

Marino, T.

ACS Catal., 2015, 10.1021/acscatal.5b00185


Metal: Rh
Ligand type: Amino acid
Anchoring strategy: Metal substitution
Optimization: ---
Reaction: Hydrogenation
Max TON: ---
ee: ---
PDB: ---
Notes: Computational study of the reaction mechanism of the formation of HCOOH from CO2

Enantioselective Transfer Hydrogenation of Ketone Catalysed by Artificial Metalloenzymes Derived from Bovine β-Lactoglobulin

Salmain, M.

Chem. Commun., 2012, 10.1039/c2cc36980j


Metal: Rh
Ligand type: Cp*; Poly-pyridine
Host protein: ß-lactoglobulin
Anchoring strategy: Supramolecular
Optimization: Chemical
Reaction: Hydrogenation
Max TON: 34
ee: 26
PDB: ---
Notes: ---

Immobilization of Two Organometallic Complexes into a Single Cage to Construct Protein-Based Microcompartment

Ueno, T.

Chem. Commun., 2016, 10.1039/C6CC00679E


Metal: Ir
Ligand type: Amino acid; Cp*
Host protein: Apo-ferritin
Anchoring strategy: Dative
Optimization: Chemical
Reaction: Hydrogenation
Max TON: ~2
ee: 15
PDB: 5E2D
Notes: Tandem reaction (Hydrogenation and Suzuki-Miyaura coupling) to form biphenylethanol from 4-iodoacetophenone and phenylboronic acid. TON and ee are given for the tandem reaction product.

Metal: Pd
Ligand type: Allyl; Amino acid
Host protein: Apo-ferritin
Anchoring strategy: Dative
Optimization: Chemical
Max TON: ~1
ee: 15
PDB: 5E2D
Notes: Tandem reaction (Hydrogenation and Suzuki-Miyaura coupling) to form biphenylethanol from 4-iodoacetophenone and phenylboronic acid.

Lipase Active Site Covalent Anchoring of Rh(NHC) Catalysts: Towards Chemoselective Artificial Metalloenzymes

Klein Gebbink, R. J. M.

Chem. Commun., 2015, 10.1039/c4cc09700a


Metal: Rh
Ligand type: Carbene
Host protein: Cutinase
Anchoring strategy: Covalent
Optimization: ---
Reaction: Hydrogenation
Max TON: 20
ee: rac.
PDB: 1CEX
Notes: ---

Metal: Rh
Ligand type: Carbene
Anchoring strategy: Covalent
Optimization: ---
Reaction: Hydrogenation
Max TON: 20
ee: rac.
PDB: 4K6G
Notes: ---

Merging Homogeneous Catalysis with Biocatalysis; Papain as Hydrogenation Catalyst

de Vries, J.

Chem. Commun., 2005, 10.1039/B512138H


Metal: Rh
Ligand type: Phosphine
Host protein: Papain (PAP)
Anchoring strategy: Covalent
Optimization: ---
Reaction: Hydrogenation
Max TON: 400
ee: <10
PDB: ---
Notes: ---

Metal-Conjugated Affinity Labels: A New Concept to Create Enantioselective Artificial Metalloenzymes

Eppinger, J.

ChemistryOpen, 2013, 10.1002/open.201200044


Metal: Rh
Ligand type: Cp*; Phosphine
Host protein: Papain (PAP)
Anchoring strategy: Covalent
Optimization: Chemical
Reaction: Hydrogenation
Max TON: 89
ee: 64
PDB: ---
Notes: ---

Metal: Ru
Ligand type: Benzene; Phosphine
Host protein: Bromelain
Anchoring strategy: Covalent
Optimization: Chemical
Reaction: Hydrogenation
Max TON: 44
ee: 20
PDB: ---
Notes: ---

Second Generation Artificial Hydrogenases Based on the Biotin- Avidin Technology: Improving Activity, Stability and Selectivity by Introduction of Enantiopure Amino Acid Spacers

Ward, T. R.

Adv. Synth. Catal., 2007, 10.1002/adsc.200700022


Metal: Rh
Ligand type: Phosphine
Host protein: Streptavidin (Sav)
Anchoring strategy: Supramolecular
Optimization: Chemical & genetic
Reaction: Hydrogenation
Max TON: ---
ee: 95
PDB: ---
Notes: ---

Second-Generation Artificial Hydrogenases Based on the Biotin-Avidin Technology: Improving Selectivity and Organic Solvent Tolerance by Introduction of an (R)-Proline Spacer

Ward, T. R.

C. R. Chim., 2007, 10.1016/j.crci.2007.02.020


Metal: Rh
Ligand type: Phosphine
Host protein: Streptavidin (Sav)
Anchoring strategy: Supramolecular
Optimization: Chemical
Reaction: Hydrogenation
Max TON: ---
ee: 94
PDB: ---
Notes: ---

Stereoselective Hydrogenation of Olefins Using Rhodium-Substituted Carbonic Anhydrase—A New Reductase

Kazlauskas, R. J.

Chem. - Eur. J., 2008, 10.1002/chem.200801673


Metal: Rh
Ligand type: COD
Anchoring strategy: Metal substitution
Optimization: Genetic
Reaction: Hydrogenation
Max TON: 15.8
ee: ---
PDB: ---
Notes: ---

Metal: Rh
Ligand type: COD
Anchoring strategy: Metal substitution
Optimization: Genetic
Reaction: Hydrogenation
Max TON: 80.5
ee: ---
PDB: 4CAC
Notes: PDB ID 4CAC = Structure of Zn containing hCAII

Synthesis of Hybrid Transition-Metalloproteins via Thiol-Selective Covalent Anchoring of Rh-Phosphine and Ru-Phenanthroline Complexes

Kamer, P. C. J.; Laan, W.

Dalton Trans., 2010, 10.1039/c0dt00239a


Metal: Rh
Ligand type: COD; Phosphine
Anchoring strategy: Covalent
Optimization: ---
Reaction: Hydrogenation
Max TON: ---
ee: ---
PDB: 2PHY
Notes: ---

Tailoring the Active Site of Chemzymes by Using a Chemogenetic-Optimization Procedure: Towards Substrate-Specific Artificial Hydrogenases Based on the Biotin–Avidin Technology

Ward, T. R.

Angew. Chem., Int. Ed., 2005, 10.1002/anie.200502000


Metal: Rh
Ligand type: Phosphine
Host protein: Streptavidin (Sav)
Anchoring strategy: Supramolecular
Optimization: Chemical & genetic
Reaction: Hydrogenation
Max TON: ---
ee: 94
PDB: ---
Notes: ---

Towards the Directed Evolution of Hybrid Catalysts

Reetz, M. T.

Chimia, 2002, 10.2533/000942902777679920


Metal: Mn
Ligand type: Salen
Host protein: Papain (PAP)
Anchoring strategy: Covalent
Optimization: ---
Reaction: Epoxidation
Max TON: ---
ee: < 10
PDB: ---
Notes: ---

Metal: Rh
Ligand type: Dipyridin-2-ylmethane
Host protein: Papain (PAP)
Anchoring strategy: Covalent
Optimization: ---
Reaction: Hydrogenation
Max TON: ---
ee: < 10
PDB: ---
Notes: ---