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Host protein

6-Phospho-gluconolactonase (6-PGLac) A2A adenosine receptor Adipocyte lipid binding protein (ALBP) Antibody Antibody 03-1 Antibody 12E11G Antibody 13G10 Antibody 13G10 / 14H7 Antibody 14H7 Antibody 1G8 Antibody 28F11 Antibody 38C2 Antibody 3A3 Antibody 7A3 Antibody7G12-A10-G1-A12 Antibody L-chain from Mab13-1 hybridoma cells Antibody SN37.4 Apo-[Fe]-hydrogenase from M. jannaschii Apo-ferritin Apo-HydA1 ([FeFe]-hydrogenase) from C. reinhardtii Apo-HydA enzymes from C. reinhardtii, M. elsdenii, C. pasteurianum Artificial construct Avidin (Av) Azurin Binding domain of Rabenosyn (Rab4) Bovine carbonic anhydrase (CA) Bovine carbonic anhydrase II (CA) Bovine serum albumin (BSA) Bovine β-lactoglobulin (βLG) Bromelain Burkavidin C45 (c-type cytochrome maquette) Carbonic anhydrase (CA) Carboxypeptidase A Catabolite activator protein (CAP) CeuE C-terminal domain of calmodulin Cutinase Cytochrome b562 Cytochrome BM3h Cytochrome c Cytochrome c552 Cytochrome cb562 Cytochrome c peroxidase Cytochrome P450 (CYP119) Domain of Hin recombinase Due Ferro 1 E. coli catabolite gene activator protein (CAP) [FeFe]-hydrogenase from C. pasteurianum (CpI) Ferredoxin (Fd) Ferritin FhuA FhuA ΔCVFtev Flavodoxin (Fld) Glyoxalase II (Human) (gp27-gp5)3 gp45 [(gp5βf)3]2 Heme oxygenase (HO) Hemoglobin Horse heart cytochrome c Horseradish peroxidase (HRP) Human carbonic anhydrase Human carbonic anhydrase II (hCAII) Human retinoid-X-receptor (hRXRa) Human serum albumin (HSA) HydA1 ([FeFe]-hydrogenase) from C. reinhardtii IgG 84A3 Laccase Lipase B from C. antarctica (CALB) Lipase from G. thermocatenulatus (GTL) LmrR Lysozyme Lysozyme (crystal) Mimochrome Fe(III)-S6G(D)-MC6 (De novo designed peptide) Mouse adenosine deaminase Myoglobin (Mb) Neocarzinostatin (variant 3.24) NikA Nitrobindin (Nb) Nitrobindin variant NB4 Nuclease from S. aureus Papain (PAP) Photoactive Yellow Protein (PYP) Photosystem I (PSI) Phytase Prolyl oligopeptidase (POP) Prolyl oligopeptidase (POP) from P. furiosus Rabbit serum albumin (RSA) Ribonuclease S RNase A Rubredoxin (Rd) Silk fibroin fibre Small heat shock protein from M. jannaschii ß-lactoglobulin Staphylococcal nuclease Steroid Carrier Protein 2L (SCP 2L) Sterol Carrier Protein (SCP) Streptavidin (monmeric) Streptavidin (Sav) Thermolysin Thermosome (THS) tHisF TM1459 cupin TRI peptide Trypsin Tryptophan gene repressor (trp) Xylanase A (XynA) Zn8:AB54 Zn8:AB54 (mutant C96T) α3D peptide α-chymotrypsin β-lactamase β-lactoglobulin (βLG)

Corresponding author

Akabori, S. Alberto, R. Albrecht, M. Anderson, J. L. R. Apfel, U.-P. Arnold, F. H. Artero, V. Bäckvall, J. E. Baker, D. Ball, Z. T. Banse, F. Berggren, G. Bian, H.-D. Birnbaum, E. R. Borovik, A. S. Bren, K. L. Bruns, N. Brustad, E. M. Cardona, F. Case, M. A. Cavazza, C. Chan, A. S. C. Coleman, J. E. Craik, C. S. Creus, M. Cuatrecasas, P. Darnall, D. W. DeGrado, W. F. Dervan, P. B. de Vries, J. Diéguez, M. Distefano, M. D. Don Tilley, T. Duhme-Klair, A. K. Ebright, R. H. Emerson, J. P. Eppinger, J. Fasan, R. Filice, M. Fontecave, M. Fontecilla-Camps, J. C. Fruk, L. Fujieda, N. Fussenegger, M. Gademann, K. Gaggero, N. Germanas, J. P. Ghattas, W. Ghirlanda, G. Golinelli-Pimpaneau, B. Goti, A. Gras, E. Gray, H. B. Green, A. P. Gross, Z. Gunasekeram, A. Happe, T. Harada, A. Hartwig, J. F. Hasegawa, J.-Y. Hayashi, T Hemschemeier, A. Herrick, R. S. Hilvert, D. Hirota, S. Huang, F.-P. Hureau, C. Hu, X. Hyster, T. K. Imanaka, T. Imperiali, B. Itoh, S. Janda, K. D. Jarvis, A. G. Jaussi, R. Jeschek, M. Kaiser, E. T. Kamer, P. C. J. Kazlauskas, R. J. Keinan, E. Khare, S. D. Kim, H. S. Kitagawa, S. Klein Gebbink, R. J. M. Kokubo, T. Korendovych, I. V. Kuhlman, B. Kurisu, G. Laan, W. Lee, S.-Y. Lehnert, N. Leow, T. C. Lerner, R. A. Lewis, J. C. Liang, H. Lindblad, P. Lin, Y.-W. Liu, J. Lombardi, A. Lubitz, W. Lu, Y. Maglio, O. Mahy, J.-P. Mangiatordi, G. F. Marchetti, M. Maréchal, J.-D. Marino, T. Marshall, N. M. Matile, S. Matsuo, T. McNaughton, B. R. Ménage, S. Messori, L. Mulfort, K. L. Nastri, F. Nicholas, K. M. Niemeyer, C. M. Nolte, R. J. M. Novič, M. Okamoto, Y. Okano, M. Okuda, J. Onoda, A. Oohora, K. Palomo, J. M. Pàmies, O. Panke, S. Pan, Y. Paradisi, F. Pecoraro, V. L. Pordea, A. Reetz, M. T. Reijerse, E. Renaud, J.-L. Ricoux, R. Rimoldi, I. Roelfes, G. Rovis, T. Sakurai, S. Salmain, M. Sasaki, T. Sauer, D. F. Schultz, P. G. Schwaneberg, U. Seelig, B. Shafaat, H. S. Shahgaldian, P. Sheldon, R. A. Shima, S. Sigman, D. S. Song, W. J. Soumillion, P. Strater, N. Sugiura, Y. Szostak, J. W. Tezcan, F. A. Thorimbert, S. Tiede, D. M. Tiller, J. C. Turner, N. J. Ueno, T. Utschig, L. M. van Koten, G. Wang, J. Ward, T. R. Watanabe, Y. Whitesides, G. M. Wilson, K. S. Woolfson, D. N. Yilmaz, F. Zhang, J.-L.

Journal

3 Biotech Acc. Chem. Res. ACS Catal. ACS Cent. Sci. ACS Sustainable Chem. Eng. Adv. Synth. Catal. Angew. Chem., Int. Ed. Appl. Biochem. Biotechnol. Appl. Organomet. Chem. Artificial Metalloenzymes and MetalloDNAzymes in Catalysis: From Design to Applications Beilstein J. Org. Chem. Biochemistry Biochim. Biophys. Acta, Bioenerg. Biochimie Bioconjug. Chem. Bioorg. Med. Chem. Bioorg. Med. Chem. Lett. Bioorganometallic Chemistry: Applications in Drug Discovery, Biocatalysis, and Imaging Biopolymers Biotechnol. Adv. Biotechnol. Bioeng. Can. J. Chem. Catal. Lett. Catal. Sci. Technol. Cat. Sci. Technol. ChemBioChem ChemCatChem Chem. Commun. Chem. Rev. Chem. Sci. Chem. Soc. Rev. Chem. - Eur. J. Chem. - Asian J. Chem. Lett. ChemistryOpen ChemPlusChem Chimia Commun. Chem. Comprehensive Inorganic Chemistry II Comprehensive Supramolecular Chemistry II C. R. Chim. Coordination Chemistry in Protein Cages: Principles, Design, and Applications Coord. Chem. Rev. Croat. Chem. Acta Curr. Opin. Biotechnol. Curr. Opin. Chem. Biol. Curr. Opin. Struct. Biol. Dalton Trans. Effects of Nanoconfinement on Catalysis Energy Environ. Sci. Eur. J. Biochem. Eur. J. Inorg. Chem. FEBS Lett. Helv. Chim. Acta Inorg. Chim. Acta Inorg. Chem. Int. J. Mol. Sci. Isr. J. Chem. J. Biol. Chem. J. Biol. Inorg. Chem. J. Immunol. Methods J. Inorg. Biochem. J. Mol. Catal. A: Chem. J. Mol. Catal. B: Enzym. J. Organomet. Chem. J. Phys. Chem. Lett. J. Porphyr. Phthalocyanines J. Protein Chem. J. Am. Chem. Soc. J. Chem. Soc. J. Chem. Soc., Chem. Commun. Methods Enzymol. Mol. Divers. Molecular Encapsulation: Organic Reactions in Constrained Systems Nature Nat. Catal. Nat. Chem. Biol. Nat. Chem. Nat. Commun. Nat. Protoc. Nat. Rev. Chem. New J. Chem. Org. Biomol. Chem. Plos ONE Proc. Natl. Acad. Sci. U. S. A. Process Biochem. Prog. Inorg. Chem. Prot. Eng. Protein Engineering Handbook Protein Expression Purif. Pure Appl. Chem. RSC Adv. Science Small Synlett Tetrahedron Tetrahedron: Asymmetry Tetrahedron Lett. Chem. Rec. Top. Catal. Top. Organomet. Chem. Trends Biotechnol.

A Metal Ion Regulated Artificial Metalloenzyme

Regulation of enzyme activity is essential in living cells. The rapidly increasing number of designer enzymes with new-to-nature activities makes it necessary to develop novel strategies for controlling their catalytic activity. Here we present the development of a metal ion regulated artificial metalloenzyme created by combining two anchoring strategies, covalent and supramolecular, for introducing a regulatory and a catalytic site, respectively. This artificial metalloenzyme is activated in the presence of Fe2+ ions, but only marginally in the presence of Zn2+.

Metal:

Fe

Ligand type:

Bypyridine

Host protein:

LmrR

Anchoring strategy:

Covalent

Optimization:

Genetic

Max TON:

14

ee:

75

PDB:

---

Notes:

---

Metal:

Zn

Ligand type:

Bypyridine

Host protein:

LmrR

Anchoring strategy:

Covalent

Optimization:

Genetic

Max TON:

6

ee:

80

PDB:

---

Notes:

---

Artificial Metalloenzymes

Review

Notes:

Book chapter

A Well-Defined Osmium–Cupin Complex: Hyperstable Artificial Osmium Peroxygenase

Metal:

Os

Ligand type:

Amino acid

Host protein:

TM1459 cupin

Anchoring strategy:

Metal substitution

Optimization:

Genetic

Reaction:

Dihydroxylation

Max TON:

45

ee:

---

PDB:

5WSE

Notes:

Exclusively cis dihydroxylation product obtained

Metal:

Os

Ligand type:

Amino acid

Host protein:

TM1459 cupin

Anchoring strategy:

Metal substitution

Optimization:

Genetic

Reaction:

Dihydroxylation

Max TON:

45

ee:

---

PDB:

5WSE

Notes:

Exclusively cis dihydroxylation product obtained

Beyond Iron: Iridium-Containing P450 Enzymes for Selective Cyclopropanations of Structurally Diverse Alkenes

Metal:

Ir

Ligand type:

Methyl; Porphyrin

Host protein:

Cytochrome P450 (CYP119)

Anchoring strategy:

Metal substitution

Optimization:

Chemical & genetic

Reaction:

Cyclopropanation

Max TON:

10181

ee:

98

PDB:

---

Notes:

Selectivity for cis product (cis/trans = 90:1)

Catalytic Cyclopropanation by Myoglobin Reconstituted with Iron Porphycene: Acceleration of Catalysis due to Rapid Formation of the Carbene Species

Metal:

Fe

Ligand type:

Amino acid; Porphycene

Host protein:

Myoglobin (Mb)

Anchoring strategy:

Reconstitution

Optimization:

---

Reaction:

Cyclopropanation

Max TON:

---

ee:

---

PDB:

---

Notes:

Cyclopropanation of styrene with ethyl diazoacetate: kcat/KM = 1.3 mM-1 * s-1, trans/cis = 99:1

Catalytic Water Oxidation by Iridium-Modified Carbonic Anhydrase

Metal:

Ir

Ligand type:

Amino acid

Anchoring strategy:

Metal substitution

Optimization:

Chemical

Reaction:

Water oxidation

Max TON:

---

ee:

---

PDB:

---

Notes:

Sodium periodate as sacrificial oxidant. TOF at pH 7 and 30°C is 39.8 min-1.

Chalcogenide Substitution in the [2Fe] Cluster of [FeFe]-Hydrogenases Conserves High Enzymatic Activity

Metal:

Fe

Ligand type:

CN; CO; Diselenolate

Anchoring strategy:

Dative

Optimization:

Chemical

Reaction:

H2 evolution

Max TON:

---

ee:

---

PDB:

5OEF

Notes:

---

Chemoselective, Enzymatic C−H Bond Amination Catalyzed by a Cytochrome P450 Containing an Ir(Me)-PIX Cofactor

Metal:

Ir

Ligand type:

Methyl; Porphyrin

Host protein:

Cytochrome P450 (CYP119)

Anchoring strategy:

Metal substitution

Optimization:

Chemical & genetic

Reaction:

C-H activation

Max TON:

294

ee:

26

PDB:

---

Notes:

---

Metal:

Ir

Ligand type:

Methyl; Porphyrin

Host protein:

Cytochrome P450 (CYP119)

Anchoring strategy:

Metal substitution

Optimization:

Chemical & genetic

Reaction:

C-H activation

Max TON:

192

ee:

95

PDB:

---

Notes:

---

Construction and In Vivo Assembly of a Catalytically Proficient and Hyperthermostable De Novo Enzyme

Metal:

Fe

Ligand type:

Porphyrin

Anchoring strategy:

Supramolecular

Optimization:

Genetic

Reaction:

Oxidation

Max TON:

---

ee:

---

PDB:

---

Notes:

Oxidation of 2,2′-azino-bis(3-ethylbenzothiazo-line-6-sulfonic acid (ABTS)

Cross-Linked Artificial Enzyme Crystals as Heterogeneous Catalysts for Oxidation Reactions

Metal:

Fe

Ligand type:

---

Host protein:

NikA

Anchoring strategy:

Supramolecular

Optimization:

Chemical

Max TON:

28000

ee:

---

PDB:

5ON0

Notes:

Cross-Linked Enzyme Crystals (CLEC) as catalysts.

Metal:

Fe

Ligand type:

---

Host protein:

NikA

Anchoring strategy:

Supramolecular

Optimization:

Chemical

Max TON:

5900

ee:

---

PDB:

5ON0

Notes:

Cross-Linked Enzyme Crystals (CLEC) as catalysts.

Cross-Regulation of an Artificial Metalloenzyme

Metal:

Ir

Ligand type:

Cp*; Phenanthroline

Host protein:

Streptavidin (Sav)

Anchoring strategy:

Supramolecular

Optimization:

Chemical & genetic

Max TON:

96

ee:

---

PDB:

---

Notes:

Cross-regulated reduction of the antibiotic enrofloxacin by an ArM.

Design of an Enantioselective Artificial Metallo-Hydratase Enzyme Containing an Unnatural Metal-Binding Amino Acid

Metal:

Cu

Ligand type:

Bipyridine

Host protein:

LmrR

Anchoring strategy:

---

Optimization:

Genetic

Reaction:

Hydration

Max TON:

9

ee:

64

PDB:

---

Notes:

---

Design of Artificial Metalloproteins/Metalloenzymes by Tuning Noncovalent Interactions

Review

Notes:

---

Diruthenium Diacetate-Catalyzed Aerobic Oxidation of Hydroxylamines and Improved Chemoselectivity by Immobilization to Lysozyme

Metal:

Ru

Ligand type:

Amino acid; OAc

Host protein:

Lysozyme

Anchoring strategy:

Dative

Optimization:

Chemical

Max TON:

1000

ee:

---

PDB:

---

Notes:

---

Enzyme Activity by Design: An Artificial Rhodium Hydroformylase for Linear Aldehydes

Metal:

Rh

Ligand type:

Acac; Diphenylphosphine

Anchoring strategy:

Cystein-maleimide

Optimization:

Chemical & genetic

Reaction:

Hydroformylation

Max TON:

409

ee:

---

PDB:

---

Notes:

Selectivity for the linear product over the branched product

Enzyme stabilization via computationally guided protein stapling

Metal:

Fe

Ligand type:

Porphyrin

Host protein:

Myoglobin (Mb)

Anchoring strategy:

Supramolecular

Optimization:

Chemical & genetic

Reaction:

Cyclopropanation

Max TON:

4740

ee:

99.2

PDB:

---

Notes:

Stapling of protein via thioether bond formation between the noncanonical amino acid O-2-bromoethyl tyrosine and cysteine

Exploiting and Engineering Hemoproteins for Abiological Carbene and Nitrene Transfer Reactions

Review

Notes:

---

Importance of Scaffold Flexibility/Rigidity in the Design and Directed Evolution of Artificial Metallo-β-Lactamases

Metal:

Zn

Ligand type:

Amino acid

Host protein:

Zn8:AB54

Anchoring strategy:

Dative

Optimization:

Genetic

Reaction:

Hydrolysis

Max TON:

---

ee:

---

PDB:

5XZI

Notes:

Supramolecular protein scaffold constructed from cytochrome cb562 building blocks, Ampicillin hydrolysis: kcat/KM = 130 min-1 * M-1

Metal:

Zn

Ligand type:

Amino acid

Host protein:

Zn8:AB54 (mutant C96T)

Anchoring strategy:

Dative

Optimization:

Genetic

Reaction:

Hydrolysis

Max TON:

---

ee:

---

PDB:

5XZI

Notes:

Supramolecular protein scaffold constructed from cytochrome cb562 building blocks, Ampicillin hydrolysis: kcat/KM = 210 min-1 * M-1

Manganese(V) Porphycene Complex Responsible for Inert C–H Bond Hydroxylation in a Myoglobin Matrix

Metal:

Mn

Ligand type:

Amino acid; Porphycene

Host protein:

Myoglobin (Mb)

Anchoring strategy:

Reconstitution

Optimization:

---

Reaction:

Hydroxylation

Max TON:

13

ee:

---

PDB:

5YL3

Notes:

---

Orthogonal Expression of an Artificial Metalloenzyme for Abiotic Catalysis

Metal:

Ir

Ligand type:

Methyl; Porphyrin

Host protein:

Cytochrome BM3h

Anchoring strategy:

Reconstitution

Optimization:

Chemical & genetic

Reaction:

Cyclopropanation

Max TON:

339

ee:

97

PDB:

---

Notes:

Reaction of styrene with ethyl diazoacetate, cis:trans = 29:71

Peroxide Activation Regulated by Hydrogen Bonds within Artificial Cu Proteins

Metal:

Cu

Host protein:

Streptavidin (Sav)

Anchoring strategy:

Supramolecular

Optimization:

Chemical & genetic

Reaction:

Oxidation

Max TON:

---

ee:

---

PDB:

6ANX

Notes:

---

Selective C–H Bond Functionalization Using Repurposed or Artificial Metalloenzymes

Review

Notes:

---

Stereoselective Sulfoxidation Catalyzed by Achiral Schiff Base Complexes in the Presence of Serum Albumin in Aqueous Media

Metal:

Co

Anchoring strategy:

Undefined

Optimization:

---

Reaction:

Sulfoxidation

Max TON:

~60

ee:

59

PDB:

---

Notes:

---

Supramolecular Anchoring of NCN-Pincer Palladium Complexes into a β-Barrel Protein Host: Molecular-Docking and Reactivity Insights

Metal:

Pd

Ligand type:

NCN-Pincer (amines)

Host protein:

β-lactoglobulin (βLG)

Anchoring strategy:

Supramolecular

Optimization:

Chemical

Reaction:

Aldol condensation

Max TON:

4.9

ee:

0

PDB:

---

Notes:

Aldol condensation of methyl isocyanoacetate and benzaldehyde (trans/cis = 38:62)

Supramolecular Enzyme Mimics

Review

Notes:

Book chapter