Literature DB >> 26244814

Synthetic heme/copper assemblies: toward an understanding of cytochrome c oxidase interactions with dioxygen and nitrogen oxides.

Shabnam Hematian1, Isaac Garcia-Bosch1, Kenneth D Karlin1.   

Abstract

Our long-time niche in synthetic biological inorganic chemistry has been to design ligands and generate coordination complexes of copper or iron ions or both, those reacting with dioxygen (O2) or nitrogen oxides (e.g., nitric oxide (NO(g)) and nitrite (NO2(-))) or both. As inspiration for this work, we turn to mitochondrial cytochrome c oxidase, which is responsible for dioxygen consumption and is also the predominant target for NO(g) and nitrite within mitochondria. In this Account, we highlight recent advances in studying synthetic heme/Cu complexes in two respects. First, there is the design, synthesis, and characterization of new O2 adducts whose further study will add insights into O2 reductive cleavage chemistry. Second, we describe how related heme/Cu constructs reduce nitrite ion to NO(g) or the reverse, oxidize NO(g) to nitrite. The reactions of nitrogen oxides occur as part of CcO's function, which is intimately tied to cellular O2 balance. We had first discovered that reduced heme/Cu compounds react with O2 giving μ-oxo heme-Fe(III)-O-Cu(II)(L) products; their properties are discussed. The O-atom is derived from dioxygen, and interrogations of these systems led to the construction and characterization of three distinctive classes of heme-peroxo complexes, two high-spin and one low-spin species. Recent investigations include a new approach to the synthesis of low-spin heme-peroxo-Cu complexes, employing a "naked" synthon, where the copper ligand denticity and geometric types can be varied. The result is a collection of such complexes; spectroscopic and structural features (by DFT calculations) are described. Some of these compounds are reactive toward reductants/protons effecting subsequent O-O cleavage. This points to how subtle improvements in ligand environment lead to a desired local structure and resulting optimized reactivity, as known to occur at enzyme active sites. The other sector of research is focused on heme/Cu assemblies mediating the redox interplay between nitrite and NO(g). In the nitrite reductase chemistry, the cupric center serves as a Lewis acid, while the heme is the redox active center providing the electron. The orientation of nitrite in approaching the ferrous heme center and N-atom binding are important. Also, detailed spectroscopic and kinetic studies of the NO(g) oxidase chemistry, in excellent agreement with theoretical calculations, reveal the intermediates and key mechanistic steps. Thus, we suggest that both chemical and biochemical heme/Cu-mediated nitrite reductase and NO(g) oxidase chemistry require N-atom binding to a ferrous heme along with cupric ion O-atom coordination, proceeding via a three-membered O-Fe-N chelate ring transition state. These important mechanistic features of heme/Cu systems interconverting NO(g) and nitrite are discussed for the first time.

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Year:  2015        PMID: 26244814      PMCID: PMC4779337          DOI: 10.1021/acs.accounts.5b00265

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN: 0001-4842            Impact factor:   22.384


  26 in total

1.  Cytochrome c oxidase rapidly metabolises nitric oxide to nitrite.

Authors:  J Torres; M A Sharpe; A Rosquist; C E Cooper; M T Wilson
Journal:  FEBS Lett       Date:  2000-06-23       Impact factor: 4.124

2.  Mitochondrial cytochrome oxidase produces nitric oxide under hypoxic conditions: implications for oxygen sensing and hypoxic signaling in eukaryotes.

Authors:  Pablo R Castello; Pamela S David; Travis McClure; Zachary Crook; Robert O Poyton
Journal:  Cell Metab       Date:  2006-04       Impact factor: 27.287

Review 3.  Binding and activation of nitrite and nitric oxide by copper nitrite reductase and corresponding model complexes.

Authors:  Anna C Merkle; Nicolai Lehnert
Journal:  Dalton Trans       Date:  2011-09-15       Impact factor: 4.390

4.  The structure of a ferrous heme-nitro species in the binuclear heme a3/CuB center of ba3-cytochrome c oxidase as determined by resonance Raman spectroscopy.

Authors:  Andreas Loullis; Mohamed Radzi Noor; Tewfik Soulimane; Eftychia Pinakoulaki
Journal:  Chem Commun (Camb)       Date:  2014-11-18       Impact factor: 6.222

Review 5.  Copper active sites in biology.

Authors:  Edward I Solomon; David E Heppner; Esther M Johnston; Jake W Ginsbach; Jordi Cirera; Munzarin Qayyum; Matthew T Kieber-Emmons; Christian H Kjaergaard; Ryan G Hadt; Li Tian
Journal:  Chem Rev       Date:  2014-03-03       Impact factor: 60.622

6.  Spectroscopic elucidation of a new heme/copper dioxygen structure type: implications for O···O bond rupture in cytochrome c oxidase.

Authors:  Matthew T Kieber-Emmons; Munzarin F Qayyum; Yuqi Li; Zakaria Halime; Keith O Hodgson; Britt Hedman; Kenneth D Karlin; Edward I Solomon
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-16       Impact factor: 15.336

7.  Nitric oxide generation from heme/copper assembly mediated nitrite reductase activity.

Authors:  Shabnam Hematian; Maxime A Siegler; Kenneth D Karlin
Journal:  J Biol Inorg Chem       Date:  2014-01-16       Impact factor: 3.358

8.  Toward a chemical mechanism of proton pumping by the B-type cytochrome c oxidases: application of density functional theory to cytochrome ba3 of Thermus thermophilus.

Authors:  James A Fee; David A Case; Louis Noodleman
Journal:  J Am Chem Soc       Date:  2008-10-17       Impact factor: 15.419

9.  Reactivity studies on Fe(III)-(O2(2-))-Cu(II) compounds: influence of the ligand architecture and copper ligand denticity.

Authors:  Eduardo E Chufán; Biplab Mondal; Thirumanavelan Gandhi; Eunsuk Kim; Nick D Rubie; Pierre Moënne-Loccoz; Kenneth D Karlin
Journal:  Inorg Chem       Date:  2007-07-06       Impact factor: 5.165

10.  A "naked" Fe(III)-(O₂²⁻)-Cu(II) species allows for structural and spectroscopic tuning of low-spin heme-peroxo-Cu complexes.

Authors:  Isaac Garcia-Bosch; Suzanne M Adam; Andrew W Schaefer; Savita K Sharma; Ryan L Peterson; Edward I Solomon; Kenneth D Karlin
Journal:  J Am Chem Soc       Date:  2015-01-16       Impact factor: 15.419

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  23 in total

1.  Isocyanide or nitrosyl complexation to hemes with varying tethered axial base ligand donors: synthesis and characterization.

Authors:  Savita K Sharma; Hyun Kim; Patrick J Rogler; Maxime A Siegler; Kenneth D Karlin
Journal:  J Biol Inorg Chem       Date:  2016-06-27       Impact factor: 3.358

Review 2.  Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Authors:  Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal:  Chem Rev       Date:  2019-01-30       Impact factor: 60.622

Review 3.  Design and engineering of artificial oxygen-activating metalloenzymes.

Authors:  Flavia Nastri; Marco Chino; Ornella Maglio; Ambika Bhagi-Damodaran; Yi Lu; Angela Lombardi
Journal:  Chem Soc Rev       Date:  2016-06-24       Impact factor: 54.564

4.  Factors That Control the Reactivity of Cobalt(III)-Nitrosyl Complexes in Nitric Oxide Transfer and Dioxygenation Reactions: A Combined Experimental and Theoretical Investigation.

Authors:  Pankaj Kumar; Yong-Min Lee; Lianrui Hu; Jianwei Chen; Young Jun Park; Jiannian Yao; Hui Chen; Kenneth D Karlin; Wonwoo Nam
Journal:  J Am Chem Soc       Date:  2016-06-07       Impact factor: 15.419

Review 5.  Oxygen Activation and Radical Transformations in Heme Proteins and Metalloporphyrins.

Authors:  Xiongyi Huang; John T Groves
Journal:  Chem Rev       Date:  2017-12-29       Impact factor: 60.622

Review 6.  Copper-Oxygen Complexes Revisited: Structures, Spectroscopy, and Reactivity.

Authors:  Courtney E Elwell; Nicole L Gagnon; Benjamin D Neisen; Debanjan Dhar; Andrew D Spaeth; Gereon M Yee; William B Tolman
Journal:  Chem Rev       Date:  2017-01-19       Impact factor: 60.622

7.  Mechanistic Insight into the Nitric Oxide Dioxygenation Reaction of Nonheme Iron(III)-Superoxo and Manganese(IV)-Peroxo Complexes.

Authors:  Seungwoo Hong; Pankaj Kumar; Kyung-Bin Cho; Yong-Min Lee; Kenneth D Karlin; Wonwoo Nam
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-04       Impact factor: 15.336

8.  Why copper is preferred over iron for oxygen activation and reduction in haem-copper oxidases.

Authors:  Ambika Bhagi-Damodaran; Matthew A Michael; Qianhong Zhu; Julian Reed; Braddock A Sandoval; Evan N Mirts; Saumen Chakraborty; Pierre Moënne-Loccoz; Yong Zhang; Yi Lu
Journal:  Nat Chem       Date:  2016-11-07       Impact factor: 24.427

9.  A High-Valent Non-Heme μ-Oxo Manganese(IV) Dimer Generated from a Thiolate-Bound Manganese(II) Complex and Dioxygen.

Authors:  Deborah Brazzolotto; Fabián G Cantú Reinhard; Julian Smith-Jones; Marius Retegan; Lucia Amidani; Abayomi S Faponle; Kallol Ray; Christian Philouze; Sam P de Visser; Marcello Gennari; Carole Duboc
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-09       Impact factor: 15.336

10.  The secondary coordination sphere and axial ligand effects on oxygen reduction reaction by iron porphyrins: a DFT computational study.

Authors:  Takehiro Ohta; Perumandla Nagaraju; Jin-Gang Liu; Takashi Ogura; Yoshinori Naruta
Journal:  J Biol Inorg Chem       Date:  2016-08-09       Impact factor: 3.358

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