137
Views
9
CrossRef citations to date
0
Altmetric
Original Articles

HYDROGENASE ACTIVE SITES: A NEW PARADIGM FOR NATURAL PRODUCT-INSPIRED SYNTHESIS BASED ON ORGANOMETALLIC CHEMISTRY

Pages 144-152 | Published online: 25 Nov 2010

REFERENCES

  • Stone , F. Gordon A. 1993 . Leaving No Stone Unturned: Pathways In Organometallic Chemistry , American Chemical Society , Washington , DC .
  • (a) Krautler , Bernhard. 2009 . Organometallic chemistry of B12 coenzymes . In Metal Ions in Life Sciences, Vol. 6: Metal-Carbon Bonds in Enzymes and Cofactors , Astrid , Sigel , Helmut , Sigel , and Roland K. O. Sigel (eds.), p. 1 – 51 , The Royal Society of Chemistry , Cambridge , UK ; (b) Matthews , Rowena G. 2009 . Cobalamin- and corrinoid-dependent enzymes . In Metal Ions in Life Sciences, Vol. 6: Metal-Carbon Bonds in Enzymes and Cofactors , Astrid , Sigel , Helmut , Sigel and Roland K. O. Sigel (eds.), p. 53 – 114 , The Royal Society of Chemistry , Cambridge , UK .
  • Bagley , Kimberly A. , Carla J. Van Garderen , Min Chen , William H. Woodruff , Evert C. Duin , and Simon P. J. Albracht . 1994 . Infrared studies on the interaction of carbon monoxide with divalent nickel in hydrogenase from chromatium vinosum . Biochemistry , 33 : 9229 – 9236 .
  • Happe , Randolph , Winfried Rosenboom , Antonio J. Pierik , Simon P. J. Albracht , and Kimberly A. Bagley . 1997 . Biological activation of hydrogen . Nature , 385 : 126 .
  • Volbeda , Anne , Marie-Helene Charon , Claudine Piras , E. Claude Hatchikian , Michel Frey , and Juan C. Fontecilla-Camps . 1995. Crystal structure of the nickel-iron hydrogenase from Desulfovibrio gigas. Nature , 373: 580–587.
  • Montet , Yael , Patricia Amara , Anne Volbeda , Xavier Vernede , E. Claude Hatchikian , Martin J. Field , Michel Frey , and Juan C. Fontecilla-Camps . 1997 . Gas access to the active site of Ni-Fe hydrogenases probed by X-ray crystallography and molecular dynamics . Nat. Struct. Biol. , 4 : 523 – 526 .
  • Darensbourg , Donald J. , Joseph H. Reibenspies , Chia-Huei Lai , Way-Zen Lee , and Marcetta Y. Darensbourg . 1997 . Analysis of an organometallic iron site model for the heterodimetallic unit of [NiFe]-hydrogenase . J. Am. Chem. Soc. , 119 : 7903 – 7904 .
  • Lai , Chia-Huei , Way-Zen Lee , Matthew L. Miller , Joseph H. Reibenspies , Donald J. Darensbourg , and Marcetta Y. Darensbourg . 1998 . Responses of the Fe(CN)2(CO) unit to electronic changes as related to its role in [NiFe]-hydrogenase . J. Am. Chem. Soc. , 120 : 10103 – 10114 .
  • Fontecilla-Camps , Juan C. , Anne Volbeda , Christine Cavazza , and Yvain Nicolet . 2007 . Structure/function relationships of [NiFe]- and [FeFe]-hydrogenases . Chem. Rev. , 107 : 4273 – 4303 .
  • Ogata , Hideaki , Wolfgand Lubitz , and Yoshiki Higuchi . 2009 . [NiFe] hydrogenases: structural and spectroscopic studies of the reaction mechanism . Dalton Trans. , 37 : 7577 – 7587 .
  • Nicolet , Yvain , Brian J. Lemon , Juan C. Fontecilla-Camps , and John W. Peters . 2000 . A novel FeS cluster in Fe-only hydrogenases . Trends in Biochemical Sciences , 25 : 138 – 143 .
  • (a) Shima , Seigo and Rolf K. Thauer . 2007 . A third type of hydrogenase catalyzing H2 activation . Chem. Rec. , 7 : 37 – 46 ; (b) Hiromoto , Takeshi , Kenichi Ataka , Oliver Pilak , Sonja Vogt , Marco Salomone Stagni , Wolfram Meyer-Klaucke , Eberhard Warkentin , Rudolf K. Thauer , Seigo Shima , and Ulrich Ermler . 2009 . The crystal structure of C176A mutated [Fe]-hydrogenase suggests an acyl-iron ligation in the active site iron complex . FEBS Letters , 583 : 585 – 590 ; (c) Shima , Seigo , Oliver Pilak , Sonja Vogt , Michael Schick , Marco S. Stagni , Wolfram Meyer-Klaucke , Eberhard Warkentin , Rudolf K. Thauer , and Ulrich Ermler . 2008 . The crystal structure of [Fe]-hydrogenase reveals the geometry of the active site . Science , 321 , 572 – 575 .
  • Chen , Dafa , Rosario Scopelliti , and Xile Hu . 2010 . Synthesis and reactivity of iron acyl complexes modeling the active site of [Fe]-hydrogenase . J. Am. Chem. Soc. , 132 : 928 – 929 .
  • Royer , Aaron M. , Thomas B. Rauchfuss , and Danielle L. Gray . 2009 . Oxidative addition to thioesters to iron(0): Active-site models for hmd, nature's third hydrogenase . Organometallics , 28 : 3618 – 3620 .
  • Turrell , Peter J. , Joseph A. Wright , Jamie N. T. Peck , Vasily S. Oganesyan , and Christopher J. Pickett . 2010. The third hydrogenase: a ferracyclic carbamoyl with close structural analogy to the active site of hmd. Angew. Chem. Int. Ed. , (in press).
  • Liaw , Wen-Feng , Nan-Hung Lee , Chien-Hong Chen , Chien-Ming Lee , Gene-Hsiang Lee , and Shie-Ming Peng . 2000 . Dinuclear and mononuclear iron(II)-thiolate complexes with mixed CO/CN- ligands: synthetic advances for iron sites of [Fe]-only hydrogenases . J. Am. Chem. Soc. , 122 : 488 – 494 .
  • Herebian , Diran , Eberhard Bothe , Eckhard Bill , Thomas Weyhermüller , and Karl Wieghardt . 2001 . Experimental evidence for the noninnocence of o-aminothiophenolates: Coordination chemistry of o-iminothionebenzosemiquinonate(1-) π-radicals with Ni(II), Pd(II), Pt(II) . J. Am. Chem. Soc. , 123 : 10012 – 10023 .
  • Liu , Tianbiao , Bin Li , Codrina V. Popescu , Andrey Bilko , Lisa M. Pérez , Michael B. Hall , and Marcetta Y. Darensbourg . 2010 . Analysis of a pentacoordinate iron dicarbonyl as synthetic analogue of the hmd or mono-iron hydrogenase active site . Chem.- A Eur. Journal , 16 : 3083 – 3089 .
  • Singleton , Michael L. , Joseph H. Reibenspies , and Marcetta Y. Darensbourg . 2010 . A cyclodextrin host/guest approach to a hydrogenase active site biomimetic cavity . J. Am. Chem. Soc. , 132 : 8870 – 8871 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.