Biological and Bioinspired Inorganic N-N Bond-Forming Reactions

Overview

Journal Chem Rev

Publisher American Chemical Society

Specialty Chemistry

Date 2020 Feb 29

PMID 32108471

Citations 22

Authors

Christina Ferousi

Sean H Majer

Ida M DiMucci

Kyle M Lancaster

Affiliations

Soon will be listed here.

Abstract

The metallobiochemistry underlying the formation of the inorganic N-N-bond-containing molecules nitrous oxide (NO), dinitrogen (N), and hydrazine (NH) is essential to the lifestyles of diverse organisms. Similar reactions hold promise as means to use N-based fuels as alternative carbon-free energy sources. This review discusses research efforts to understand the mechanisms underlying biological N-N bond formation in primary metabolism and how the associated reactions are tied to energy transduction and organismal survival. These efforts comprise studies of both natural and engineered metalloenzymes as well as synthetic model complexes.

Citing Articles

Intermolecular N-N Coupling of a Dinitrosyl Iron Complex Induced by Hydrogen Bond Donors in the Secondary Coordination Sphere.

Fugami K, Black G, Kowalczyk T, Seda T, Gilbertson J J Am Chem Soc. 2025; 147(9):7274-7281.

PMID: 39969499 PMC: 11887047. DOI: 10.1021/jacs.4c12787.

Recent Developments and Challenges in the Enzymatic Formation of Nitrogen-Nitrogen Bonds.

Angeli C, Atienza-Sanz S, Schroder S, Hein A, Li Y, Argyrou A ACS Catal. 2025; 15(1):310-342.

PMID: 39781334 PMC: 11705231. DOI: 10.1021/acscatal.4c05268.

Abiotic anammox by a naturally occurring mineral.

Chaudhuri S, Warren T Nat Chem. 2024; 16(10):1574-1575.

PMID: 39349611 DOI: 10.1038/s41557-024-01635-5.

Methanobactins: Structures, Biosynthesis, and Microbial Diversity.

Reyes R, Rosenzweig A Annu Rev Microbiol. 2024; 78(1):383-401.

PMID: 39121541 PMC: 11619078. DOI: 10.1146/annurev-micro-041522-092911.

Widespread detoxifying NO reductases impart a distinct isotopic fingerprint on NO under anoxia.

Wang R, Lonergan Z, Wilbert S, Eiler J, Newman D Proc Natl Acad Sci U S A. 2024; 121(25):e2319960121.

PMID: 38865268 PMC: 11194513. DOI: 10.1073/pnas.2319960121.

References

Thorgersen M, Stirrett K, Scott R, Adams M . Mechanism of oxygen detoxification by the surprisingly oxygen-tolerant hyperthermophilic archaeon, Pyrococcus furiosus. Proc Natl Acad Sci U S A. 2012; 109(45):18547-52. PMC: 3494905. DOI: 10.1073/pnas.1208605109. View

Ghosh S, Deka H, Dangat Y, Saha S, Gogoi K, Vanka K . Reductive nitrosylation of nickel(ii) complex by nitric oxide followed by nitrous oxide release. Dalton Trans. 2016; 45(25):10200-8. DOI: 10.1039/c6dt00826g. View

Mattila K, Haltia T . How does nitrous oxide reductase interact with its electron donors?--A docking study. Proteins. 2005; 59(4):708-22. DOI: 10.1002/prot.20437. View

Xu N, Goodrich L, Lehnert N, Powell D, Richter-Addo G . Preparation of the elusive [(por)Fe(NO)(O-ligand)] complex by diffusion of nitric oxide into a crystal of the precursor. Angew Chem Int Ed Engl. 2013; 52(14):3896-900. DOI: 10.1002/anie.201208063. View

Koutny M, Kucera I, Tesarik R, Turanek J, Van Spanning R . Pseudoazurin mediates periplasmic electron flow in a mutant strain of Paracoccus denitrificans lacking cytochrome c550. FEBS Lett. 1999; 448(1):157-9. DOI: 10.1016/s0014-5793(99)00345-2. View

Gwak J, Ahn S, Baik M, Lee Y . One metal is enough: a nickel complex reduces nitrate anions to nitrogen gas. Chem Sci. 2019; 10(18):4767-4774. PMC: 6510316. DOI: 10.1039/c9sc00717b. View

Oshiki M, Ali M, Shinyako-Hata K, Satoh H, Okabe S . Hydroxylamine-dependent anaerobic ammonium oxidation (anammox) by "Candidatus Brocadia sinica". Environ Microbiol. 2016; 18(9):3133-43. DOI: 10.1111/1462-2920.13355. View

Weichsel A, Andersen J, Roberts S, Montfort W . Nitric oxide binding to nitrophorin 4 induces complete distal pocket burial. Nat Struct Biol. 2000; 7(7):551-4. DOI: 10.1038/76769. View

DellAcqua S, Moura I, Moura J, Pauleta S . The electron transfer complex between nitrous oxide reductase and its electron donors. J Biol Inorg Chem. 2011; 16(8):1241-54. DOI: 10.1007/s00775-011-0812-9. View

10.

Gronberg K, Roldan M, Prior L, Butland G, Cheesman M, Richardson D . A low-redox potential heme in the dinuclear center of bacterial nitric oxide reductase: implications for the evolution of energy-conserving heme-copper oxidases. Biochemistry. 1999; 38(42):13780-6. DOI: 10.1021/bi9916426. View

11.

Farrar J, Zumft W, Thomson A . CuA and CuZ are variants of the electron transfer center in nitrous oxide reductase. Proc Natl Acad Sci U S A. 1998; 95(17):9891-6. PMC: 21432. DOI: 10.1073/pnas.95.17.9891. View

12.

Silaghi-Dumitrescu R, Ng K, Viswanathan R, Kurtz Jr D . A flavo-diiron protein from Desulfovibrio vulgaris with oxidase and nitric oxide reductase activities. Evidence for an in vivo nitric oxide scavenging function. Biochemistry. 2005; 44(9):3572-9. DOI: 10.1021/bi0477337. View

13.

Singh U, Obayashi E, Takahashi S, Iizuka T, Shoun H, Shiro Y . The effects of heme modification on reactivity, ligand binding properties and iron-coordination structures of cytochrome P450nor. Biochim Biophys Acta. 1998; 1384(1):103-11. DOI: 10.1016/s0167-4838(98)00006-5. View

14.

Bhagi-Damodaran A, Petrik I, Lu Y . Using Biosynthetic Models of Heme-Copper Oxidase and Nitric Oxide Reductase in Myoglobin to Elucidate Structural Features Responsible for Enzymatic Activities. Isr J Chem. 2016; 56:773-790. PMC: 5161413. DOI: 10.1002/ijch.201600033. View

15.

Zumft W . Nitric oxide reductases of prokaryotes with emphasis on the respiratory, heme-copper oxidase type. J Inorg Biochem. 2004; 99(1):194-215. DOI: 10.1016/j.jinorgbio.2004.09.024. View

16.

Jiang Y, Hayashi T, Matsumura H, Do L, Majumdar A, Lippard S . Light-induced N₂O production from a non-heme iron-nitrosyl dimer. J Am Chem Soc. 2014; 136(36):12524-7. PMC: 4160282. DOI: 10.1021/ja504343t. View

17.

Iverson T, Arciero D, Hsu B, Logan M, Hooper A, Rees D . Heme packing motifs revealed by the crystal structure of the tetra-heme cytochrome c554 from Nitrosomonas europaea. Nat Struct Biol. 1998; 5(11):1005-12. DOI: 10.1038/2975. View

18.

Matsumoto Y, Tosha T, Pisliakov A, Hino T, Sugimoto H, Nagano S . Crystal structure of quinol-dependent nitric oxide reductase from Geobacillus stearothermophilus. Nat Struct Mol Biol. 2012; 19(2):238-45. DOI: 10.1038/nsmb.2213. View

19.

Kartal B, Keltjens J . Anammox Biochemistry: a Tale of Heme c Proteins. Trends Biochem Sci. 2016; 41(12):998-1011. DOI: 10.1016/j.tibs.2016.08.015. View

20.

Lu S, Libby E, Saleh L, Xing G, Bollinger Jr J, Moenne-Loccoz P . Characterization of NO adducts of the diiron center in protein R2 of Escherichia coli ribonucleotide reductase and site-directed variants; implications for the O2 activation mechanism. J Biol Inorg Chem. 2004; 9(7):818-27. DOI: 10.1007/s00775-004-0582-8. View