Artificial hydrogenases: Biohybrid and supramolecular systems for catalytic hydrogen production or uptake

Current Opinion in Chemical Biology

Volumn 25, Issue 1, 2015, Pages 36-47

  Caserta, Giorgio ^a   Roy, Souvik ^b   Atta, Mohamed ^b   Artero, Vincent ^b   Fontecave, Marc ^a,b  

^a SORBONNE UNIVERSITÉ   (France)

^b UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARTIFICIAL HYDROGENASE; COBALT COMPLEX; HYDROGEN; HYDROGENASE; IRON COMPLEX; METAL ORGANIC FRAMEWORK; NICKEL COMPLEX; OLIGOMER; POLYACRYLIC ACID; POLYMER; POLYSACCHARIDE; UNCLASSIFIED DRUG; BIOMIMETIC MATERIAL; ORGANOMETALLIC COMPOUND;

BIOHYBRID; CATALYSIS; CATALYST; ENZYME ACTIVE SITE; HYBRID; HYDROGENATION; MICELLE; POLYMERIZATION; REVIEW; SUPRAMOLECULAR CHEMISTRY; AMINO ACID SEQUENCE; CHEMISTRY; METABOLISM; MOLECULAR GENETICS;

AMINO ACID SEQUENCE; BIOMIMETIC MATERIALS; HYDROGEN; HYDROGENASE; MOLECULAR SEQUENCE DATA; ORGANOMETALLIC COMPOUNDS;

EID: 84928723435     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2014.12.018     Document Type: Review

References (49)

1. Lubitz W., Ogata H., Rudiger O., Reijerse E. Hydrogenases. Chem Rev 2014, 114:4081-4148.
2. Cracknell J.A., Vincent K.A., Armstrong F.A. Enzymes as working or inspirational electrocatalysts for fuel cells and electrolysis. Chem Rev 2008, 108:2439-2461.
3. Woolerton T.W., Sheard S., Chaudhary Y.S., Armstrong F.A. Enzymes and bio-inspired electrocatalysts in solar fuel devices. Energy Environ Sci 2012, 5:7470-7490.
4. Simmons T.R., Berggren G., Bacchi M., Fontecave M., Artero V. Mimicking hydrogenases: from biomimetics to artificial enzymes. Coord Chem Rev 2014, 270-271:127-150.
5. Artero V., Chavarot-Kerlidou M., Fontecave M. Splitting water with cobalt. Angew Chem Int Ed 2011, 50:7238-7266.
6. Artero V., Saveant J.-M. Toward the rational benchmarking of homogeneous H2-evolving catalysts. Energy Environ Sci 2014, 10.1039/c1034ee01709a.
7. Wilson M.E., Whitesides G.M. Conversion of a protein to a homogeneous asymmetric hydrogenation catalyst by site-specific modification with a diphosphinerhodium(I) moiety. J Am Chem Soc 1978, 100:306-307.
8. Durrenberger M., Ward T.R. Recent achievements in the design and engineering of artificial metalloenzymes. Curr Opin Chem Biol 2014, 19:99-106.
9. Berggren G., Adamska A., Lambertz C., Simmons T.R., Esselborn J., Atta M., Gambarelli S., Mouesca J.M., Reijerse E., Lubitz W., et al. Biomimetic assembly and activation of [FeFe]-hydrogenases. Nature 2013, 499:66-69.
10. Esselborn J., Lambertz C., Adamska-Venkatesh A., Simmons T., Berggren G., Noth J., Siebel J., Hemschemeier A., Artero V., Reijerse E., et al. Spontaneous activation of [FeFe]-hydrogenases by an inorganic [2Fe] active site mimic. Nat Chem Biol 2013, 9:607-609.
11. Roy A., Madden C., Ghirlanda G. Photo-induced hydrogen production in a helical peptide incorporating a [FeFe] hydrogenase active site mimic. Chem Commun 2012, 48:9816-9818.
12. Sano Y., Onoda A., Hayashi T. A hydrogenase model system based on the sequence of cytochrome c: photochemical hydrogen evolution in aqueous media. Chem Commun 2011, 47:8229-8231.
13. Sano Y., Onoda A., Hayashi T. Photocatalytic hydrogen evolution by a diiron hydrogenase model based on a peptide fragment of cytochrome c556 with an attached diiron carbonyl cluster and an attached ruthenium photosensitizer. J Inorg Biochem 2012, 108:159-162.
14. Wang H.-Y., Wang W.-G., Si G., Wang F., Tung C.-H., Wu L.-Z. Photocatalytic hydrogen evolution from rhenium(I) complexes to [FeFe] hydrogenase mimics in aqueous SDS micellar systems: a biomimetic pathway. Langmuir 2010, 26:9766-9771.
15. Quentel F., Passard G., Gloaguen F. A binuclear iron-thiolate catalyst for electrochemical hydrogen production in aqueous micellar solution. Chem Eur J 2012, 18:13473-13479.
16. Quentel F., Passard G., Gloaguen F. Electrochemical hydrogen production in aqueous micellar solution by a diiron benzenedithiolate complex relevant to [FeFe] hydrogenases. Energy Environ Sci 2012, 5:7757-7761.
17. Wang F., Wang W.-G., Wang H.-Y., Si G., Tung C.-H., Wu L.-Z. Artificial photosynthetic systems based on [FeFe]-hydrogenase mimics: the road to high efficiency for light-driven hydrogen evolution. ACS Catal 2012, 2:407-416.
18. Orain C., Quentel F., Gloaguen F. Photocatalytic hydrogen production using models of the iron-iron hydrogenase active site dispersed in micellar solution. ChemSusChem 2014, 7:638-643.
19. Yu T., Zeng Y., Chen J., Li Y.-Y., Yang G., Li Y. Exceptional dendrimer-based mimics of diiron hydrogenase for the photochemical production of hydrogen. Angew Chem Int Ed 2013, 52:5631-5635.
20. Wang F., Liang W.-J., Jian J.-X., Li C.-B., Chen B., Tung C.-H., Wu L.-Z. Exceptional poly(acrylic acid)-based artificial [FeFe]-hydrogenases for photocatalytic H2 production in water. Angew Chem Int Ed 2013, 52:8134-8138.
21. Singleton M.L., Reibenspies J.H., Darensbourg M.Y. A cyclodextrin host/guest approach to a hydrogenase active site biomimetic cavity. J Am Chem Soc 2010, 132:8870-8871.
22. Singleton M.L., Crouthers D.J., Duttweiler R.P., Reibenspies J.H., Darensbourg M.Y. Sulfonated diiron complexes as water-soluble models of the [Fe-Fe]-hydrogenase enzyme active site. Inorg Chem 2011, 50:5015-5026.
23. Li X., Wang M., Zheng D., Han K., Dong J., Sun L. Photocatalytic H2 production in aqueous solution with host-guest inclusions formed by insertion of an FeFe-hydrogenase mimic and an organic dye into cyclodextrins. Energy Environ Sci 2012, 5:8220-8224.
24. Jian J.-X., Liu Q., Li Z.-J., Wang F., Li X.-B., Li C.-B., Liu B., Meng Q.-Y., Chen B., Feng K., et al. Chitosan confinement enhances hydrogen photogeneration from a mimic of the diiron subsite of [FeFe]-hydrogenase. Nat Commun 2013, 4:2695.
25. Pullen S., Fei H., Orthaber A., Cohen S.M., Ott S. Enhanced photochemical hydrogen production by a molecular diiron catalyst incorporated into a metal-organic framework. J Am Chem Soc 2013, 135:16997-17003.
26. Sasan K., Lin Q., Mao C., Feng P. Incorporation of iron hydrogenase active sites into a highly stable metal-organic framework for photocatalytic hydrogen generation. Chem Commun 2014, 50:10390-10393.
27. Simmons T.R., Artero V. Catalytic hydrogen oxidation: dawn of a new iron age. Angew Chem Int Ed 2013, 52:6143-6145.
28. DuBois D.L. Development of molecular electrocatalysts for energy storage. Inorg Chem 2014, 53:3935-3960.
29. Ginovska-Pangovska B., Dutta A., Reback M.L., Linehan J.C., Shaw W.J. Beyond the active site: the impact of the outer coordination sphere on electrocatalysts for hydrogen production and oxidation. Acc Chem Res 2014, 47:2621-2630.
30. Jain A., Lense S., Linehan J.C., Raugei S., Cho H., DuBois D.L., Shaw W.J. Incorporating peptides in the outer-coordination sphere of bioinspired electrocatalysts for hydrogen production. Inorg Chem 2011, 50:4073-4085.
31. Jain A., Reback M.L., Lindstrom M.L., Thogerson C.E., Helm M.L., Appel A.M., Shaw W.J. Investigating the role of the outer-coordination sphere in [Ni(PPh2NPh-R2)2]2+ hydrogenase mimics. Inorg Chem 2012, 51:6592-6602.
32. Reback M.L., Ginovska-Pangovska B., Ho M.-H., Jain A., Squier T.C., Raugei S., Roberts J.A.S., Shaw W.J. The role of a dipeptide outer-coordination sphere on H2-production catalysts: influence on catalytic rates and electron transfer. Chem Eur J 2013, 19:1928-1941.
33. Reback M.L., Buchko G.W., Kier B.L., Ginovska-Pangovska B., Xiong Y., Lense S., Hou J., Roberts J.A.S., Sorensen C.M., Raugei S., et al. Enzyme design from the bottom up: an active nickel electrocatalyst with a structured peptide outer coordination sphere. Chem Eur J 2014, 20:1510-1514.
34. Kilgore U.J., Roberts J.A.S., Pool D.H., Appel A.M., Stewart M.P., DuBois M.R., Dougherty W.G., Kassel W.S., Bullock R.M., DuBois D.L. [Ni(PPh2NC6H4X2)2]2+ complexes as electrocatalysts for H2 production: effect of substituents, acids, and water on catalytic rates. J Am Chem Soc 2011, 133:5861-5872.
35. Shaw W.J., Helm M.L., DuBois D.L. A modular, energy-based approach to the development of nickel containing molecular electrocatalysts for hydrogen production and oxidation. Biochim Biophys Acta 2013, 1827:1123-1139.
36. Dutta A., Lense S., Hou J., Engelhard M.H., Roberts J.A.S., Shaw W.J. Minimal proton channel enables H2 oxidation and production with a water-soluble nickel-based catalyst. J Am Chem Soc 2013, 135:18490-18496.
37. Dutta A., Roberts J.A.S., Shaw W.J. Arginine-containing ligands enhance H2 oxidation catalyst performance. Angew Chem Int Ed 2014, 53:6487-6491.
38. Dutta A., DuBois D.L., Roberts J.A.S., Shaw W.J. Amino acid modified Ni catalyst exhibits reversible H2 oxidation/production over a broad pH range at elevated temperatures. Proc Natl Acad Sci USA 2014, 111:16286-16291.
39. Silver S.C., Niklas J., Du P., Poluektov O.G., Tiede D.M., Utschig L.M. Protein delivery of a Ni catalyst to photosystem I for light-driven hydrogen production. J Am Chem Soc 2013, 135:13246-13249.
40. Kleingardner J.G., Kandemir B., Bren K.L. Hydrogen evolution from neutral water under aerobic conditions catalyzed by cobalt microperoxidase-11. J Am Chem Soc 2014, 136:4-7.
41. Sommer D.J., Vaughn M.D., Ghirlanda G. Protein secondary-shell interactions enhance the photoinduced hydrogen production of cobalt protoporphyrin IX. Chem Commun 2014, 50:15852-15855.
42. Kellett R.M., Spiro T.G. Cobalt(I) porphyrin catalysts of hydrogen production from water. Inorg Chem 1985, 24:2373-2377.
43. Kellett R.M., Spiro T.G. Cobalt porphyrin electrode films as hydrogen catalysts. Inorg Chem 1985, 24:2378-2382.
44. Abe T., Taguchi F., Imaya H., Zhao F., Zhang J., Kaneko M. Highly active electrocatalysis by cobalt tetraphenylporphyrin incorporated in a Nafion membrane for proton reduction. Polym Adv Technol 1998, 9:559-562.
45. Artero V., Fontecave M. Some general principles for designing electrocatalysts with hydrogenase activity. Coord Chem Rev 2005, 249:1518-1535.
46. Yu F., Cangelosi V.M., Zastrow M.L., Tegoni M., Plegaria J.S., Tebo A.G., Mocny C.S., Ruckthong L., Qayyum H., Pecoraro V.L. Protein design: toward functional metalloenzymes. Chem Rev 2014, 114:3495-3578.
47. Bacchi M., Berggren G., Niklas J., Veinberg E., Mara M.W., Shelby M.L., Poluektov O.G., Chen L.X., Tiede D.M., Cavazza C., et al. Cobaloxime-based artificial hydrogenases. Inorg Chem 2014, 53:8071-8082.
48. Andreiadis E.S., Jacques P.-A., Tran P.D., Leyris A., Chavarot-Kerlidou M., Jousselme B., Matheron M., Pecaut J., Palacin S., Fontecave M., et al. Molecular engineering of a cobalt-based electrocatalytic nanomaterial for H2 evolution under fully aqueous conditions. Nat Chem 2013, 5:48-53.
49. Utschig L.M., Silver S.C., Mulfort K.L., Tiede D.M. Nature-driven photochemistry for catalytic solar hydrogen production: a photosystem I-transition metal catalyst hybrid. J Am Chem Soc 2011, 133:16334-16337.