Abstract
The 2-His-1-carboxylate facial triad is a widely used scaffold to bind the iron center in mononuclear nonheme iron enzymes for activating dioxygen in a variety of oxidative transformations of metabolic significance. Since the 1990s, over a hundred different iron enzymes have been identified to use this platform. This structural motif consists of two histidines and the side chain carboxylate of an aspartate or a glutamate arranged in a facial array that binds iron(II) at the active site. This triad occupies one face of an iron-centered octahedron and makes the opposite face available for the coordination of O2 and, in many cases, substrate, allowing the tailoring of the iron-dioxygen chemistry to carry out a plethora of diverse reactions. Activated dioxygen-derived species involved in the enzyme mechanisms include iron(III)-superoxo, iron(III)-peroxo, and high-valent iron(IV)-oxo intermediates. In this article, we highlight the major crystallographic, spectroscopic, and mechanistic advances of the past 20 years that have significantly enhanced our understanding of the mechanisms of O2 activation and the key roles played by iron-based oxidants.
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Abbreviations
- l-Aba:
-
l-2-Aminobutyric acid
- ACCO:
-
1-Aminocyclopropane-1-carboxylate oxidase
- ACV:
-
δ-(l-α-Aminoadipoyl)-l-cysteinyl-d-valine
- AIB:
-
(α-Aminoisobutyric acid)
- AlkB:
-
Enzymes involved in oxidative DNA and RNA repair
- AsqJ:
-
4′-Methoxyviridicatin synthase
- AsnO:
-
Asparagine oxygenase
- BH4 :
-
6(R)-l-erythro-5,6,7,8-tetrahydrobiopterin
- BphC:
-
2,3-Dihydroxybiphenyl 1,2-dioxygenase
- BZDO:
-
Benzoate 1,2-dioxygense
- BDPP:
-
2,6-Bis[[(S)-2-(diphenylhydroxymethyl)-1-pyrrolidinyl]methyl]pyridine dianion
- CarC:
-
Carbapenem synthase
- CARDO:
-
Carbazole 1,9a-dioxygenase
- CAS:
-
Clavaminate synthase
- CloR:
-
3-Dimethylallyl-4-hydroxybenzoate synthase
- l-Cpg:
-
l-Cyclopropylglycine
- Cur Hal:
-
Halogenase in the biosynthesis of curacin A
- CytC2:
-
Substrate carrier protein for CytC3 in the biosynthesis of cytotrienin
- CytC3:
-
Halogenase in the biosynthesis of cytotrienin
- DAOCS:
-
Deacetoxycephalosporin C synthase
- DdaC:
-
Epoxidase in biosynthesis of N β -epoxysuccinamoyl-DAP-Val
- DFT:
-
Density functional theory
- DMO:
-
Dicamba O-demethylase
- l-DOPA:
-
l-3,4-Dihydroxyphenylalanine
- EFE:
-
Ethylene forming enzyme
- ENDOR:
-
Electron nuclear double resonance
- EPR:
-
Electron paramagnetic resonance
- EXAFS:
-
Extended X-ray absorption fine structure
- FIH-1:
-
Factor-inhibiting hypoxia-inducible factor-1
- FtmOx1:
-
Fumitremorgin B endoperoxidase
- HEPD:
-
2-Hydroxyethylphosphonate dioxygenase
- HMS:
-
4-Hydroxymandelate synthase
- 1-HPP:
-
1-Hydroxypropylphosphonate
- 2-HPP:
-
2-Hydroxypropyl-1-phosphonate
- HPPD:
-
4-Hydroxyphenylpyruvate dioxygenase
- HppE:
-
(S)-2-Hydroxypropylphosphonate epoxidase
- HYSCORE:
-
Hyperfine sublevel correlation spectroscopy
- IPNS:
-
Isopenicillin N synthase
- α-KG:
-
α-Ketoglutarate
- KIE:
-
Kinetic isotope effect
- KshAB:
-
3-Ketosteroid 9α-hydroxylase
- MCD:
-
Magnetic circular dichroism
- NDO:
-
Naphthalene 1,2-dioxygenase
- N4Py:
-
N,N-bis(2-pyridylmethyl)-N-bis(2-pyridyl)methylamine
- NRVS:
-
Nuclear resonance vibrational spectroscopy
- l-Nva:
-
l-Norvaline
- OMO:
-
2-Oxoquinoline 8-monooxygenase
- OrfP:
-
Enzyme that catalyzes conversion of l-Arg into (3R,4R)-(OH)2-l-Arg
- P4H:
-
Prolyl-4-hydroxylase
- PenD:
-
Epoxidase in biosynthesis of pentalenolactone
- PheH:
-
Phenylalanine hydroxylase
- PrnD:
-
Aminopyrrolnitrin oxygenase
- RedG:
-
Rieske enzyme that catalyzes the oxidative carbocyclization of undecylprodigiosin to form streptorubin B
- RFQ:
-
Rapid-freeze-quench
- SIE:
-
Solvent isotope effect
- SnoK:
-
Carbocyclase in nogalamycin biosynthesis
- SnoN:
-
Epimerase in nogalamycin biosynthesis
- Stc2:
-
Stachydrine demethylase
- SyrB1:
-
Substrate carrier protein for SyrB2 in syringomycin biosynthesis
- SyrB2:
-
Halogenase in syringomycin biosynthesis
- TauD:
-
Taurine:α-KG dioxygenase
- TDO:
-
Toluene dioxygenase
- THA:
-
3-(2-Thienyl)-l-alanine
- TMC:
-
1,4,8,11-Tetramethyl-1,4,8,11-tetraazacyclotetradecane
- TQA:
-
Tris(quinolyl-2-methyl)amine
- TrpH:
-
Tryptophan hydroxylase
- TyrH:
-
Tyrosine hydroxylase
- WelO5:
-
Halogenase involved in the maturation process to form welwitindolinones
- XRD:
-
X-ray diffraction
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Acknowledgements
We thank the U. S. National Science Foundation for funding (CHE-1361773 to L.Q.) and are grateful to Dr. Caleb Allpress and Dr. Johannes E. M. N. Klein for valuable input and discussions.
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Kal, S., Que, L. Dioxygen activation by nonheme iron enzymes with the 2-His-1-carboxylate facial triad that generate high-valent oxoiron oxidants. J Biol Inorg Chem 22, 339–365 (2017). https://doi.org/10.1007/s00775-016-1431-2
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DOI: https://doi.org/10.1007/s00775-016-1431-2