Monooxygenase

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<StructureSection load='5tkh' size='350' side='right' scene='' caption='Glycosylated lytic polysaccharide monooxygenase complex with Cu(II) (orange) and peroxide (PDB code [[5tkh]])' >
<StructureSection load='5tkh' size='350' side='right' scene='' caption='Glycosylated lytic polysaccharide monooxygenase complex with Cu(II) (orange) and peroxide (PDB code [[5tkh]])' >
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__TOC__
== Function ==
== Function ==
'''Monooxygenases''' (MO) catalyzes the incorporation of a hydroxyl group into a variety of substrates. MO catalyzes the reduction of O<sub>2</sub> to H<sub>2</sub>O while oxidating NADPH.
'''Monooxygenases''' (MO) catalyzes the incorporation of a hydroxyl group into a variety of substrates. MO catalyzes the reduction of O<sub>2</sub> to H<sub>2</sub>O while oxidating NADPH.
 +
*'''ActVA-Orf6 monooxygenase''' catalyses the oxidation of an aromatic intermediate of the actinorhodin pathway <ref>PMID:12514126</ref>.
 +
*'''Baeyer-Villigen monooxygenase''' is a bioanalytic tool which can catalyze reactions which are difficult to do via chemical means<ref>PMID:15599520</ref>.
 +
*'''TropB monooxygenase''' catalyses asymmetric oxidative dearomatization reactions <ref>PMID:31346489</ref>.
 +
*'''TetX monooxygenase''' inactivates the tetracycline antibiotic <ref>PMID:15452119</ref>.
 +
*'''Phenol 2-monooxygenase''' see [[Phenol hydroxylase (hebrew)]].
=== Peptidylglycine α-Hydroxylating Monooxygenase (PHM)-coordination of peroxide to Cu<sub>M</sub> center. Structural and computational study <ref >doi 10.1007/s00775-012-0967-z</ref>===
=== Peptidylglycine α-Hydroxylating Monooxygenase (PHM)-coordination of peroxide to Cu<sub>M</sub> center. Structural and computational study <ref >doi 10.1007/s00775-012-0967-z</ref>===
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</StructureSection>
</StructureSection>
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==3D structures of monooxygenase==
 
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Updated on {{REVISIONDAY2}}-{{MONTHNAME|{{REVISIONMONTH}}}}-{{REVISIONYEAR}}
 
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{{#tree:id=OrganizedByTopic|openlevels=0|
 
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*'''Toluene 4-monooxygenase (TMO)'''
 
- 
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**[[3dhg]], [[3i5j]], [[2inc]] – PmTMO α+β+γ subunits + Fe – ''Pseudomonas mendocina''<br />
 
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**[[2ind]] – PmTMO α+β+γ subunits + Mn <br />
 
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**[[3rng]], [[3rnf]], [[3rne]], [[3rnc]], [[3rnb]], [[3rna]], [[3rn9]], [[3n20]], [[3n1z]], [[3n1y]], [[3n1x]], [[2rdb]] – PmTMO α+β+γ subunits (mutant) + Fe <br />
 
-
**[[1sjg]] – PmTMO protein C + Fe <br />
 
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**[[1vm9]] – PmTMO protein C (mutant) + Fe <br />
 
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**[[2bf5]], [[2bf3]], [[2bf2]] – PmTMO protein D <br />
 
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**[[4wqm]] – PmTMO (mutant) + Ni <br />
 
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**[[4p1c]], [[4p1b]] – PmTMO protein A+B+E+ferredoxin (mutant) + Fe <br />
 
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**[[2q3w]] – PmTMO ferredoxin subunit (mutant) + Fe <br />
 
- 
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*TMO complexes
 
- 
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**[[3dhh]], [[3q3n]], [[3q3o]] – PmTMO α+β+γ subunits + Fe + phenol derivative + TMO system effector protein<br />
 
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**[[3rmk]], [[1t0s]], [[1t0q]] – PmTMO α+β+γ subunits + Fe + phenol derivative<br />
 
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**[[3q14]] – PmTMO α+β+γ subunits + Fe + p-cresol + TMO system effector protein<br />
 
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**[[3q2a]], [[3q3m]] – PmTMO α+β+γ subunits + Fe + benzoate inhibitor + TMO system effector protein<br />
 
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**[[3dhi]] – PmTMO α+β+γ subunits + Fe + TMO system effector protein<br />
 
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**[[3ge3]], [[3ge8]], [[3ri7]] – PmTMO α (mutant)+β+γ subunits + Fe + TMO system effector protein<br />
 
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**[[3i63]] – PmTMO α+β+γ subunits + Fe + TMO system effector protein + H2O2<br />
 
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**[[5tdv]] – PmTMO protein A+B+D+E + Fe + peroxide<br />
 
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**[[5tdu]] – PmTMO protein A+B+D+E + Fe + cresol<br />
 
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**[[5tdt]] – PmTMO protein A+B+D+E + Fe + peroxide + toluene<br />
 
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**[[5tds]] – PmTMO protein A+B+D+E + Fe + toluene<br />
 
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**[[1t0r]] – PsTMO + Fe + OH – ''Pseudomonas stutzeri''<br />
 
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*'''Heme-degrading monooxygenase (IsdI)'''
 
- 
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**[[2zdp]] – SaIsdI + heme-Co – ''Staphylococcus aureus''<br />
 
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**[[3lgm]], [[2zdo]] – SaIsdI + heme-Fe<br />
 
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**[[4fnh]] – SaIsdI (mutant) + heme-Fe<br />
 
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**[[3lgn]] – SaIsdI + heme-Fe + O2<br />
 
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**[[3qgp]] – SaIsdI + heme-Fe + CN<br />
 
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**[[4fni]] – SaIsdI (mutant) + heme-Fe + CN<br />
 
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**[[4nl5]] – MtMO + heme + CN – ''Mycobacterium tuberculosis''<br />
 
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**[[4oz5]] – MO + heme – ''Bacillus subtilis''<br />
 
- 
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*'''Kynurenine 3-monooxygenase (KMO)'''
 
- 
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**[[5x68]] – hKMO + FAD - human<br />
 
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**[[4j2w]], [[4j31]], [[4j33]], [[4j34]] – yKMO + FAD – yeast<br />
 
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**[[4j36]], [[5x64]] – yKMO + FAD + inhibitor<br />
 
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**[[5x6q]] – yKMO (mutant) + FAD + inhibitor<br />
 
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**[[5na5]], [[5x6p]] – PfKMO (mutant) + FAD – ''Pseudomonas fluorescens''<br />
 
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**[[5y7a]], [[5y77]], [[6fox]] – PfKMO + FAD + kynurenine <br />
 
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**[[5nak]] – PfKMO (mutant) + FAD + kynurenine <br />
 
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**[[5y66]] – PfKMO + FAD + kynurenine + inhibitor<br />
 
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**[[6fph]], [[6fp1]], [[6fp0]], [[6foz]], [[6foy]] – PfKMO + FAD + inhibitor<br />
 
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**[[5nah]], [[5nag]], [[5nae]], [[5nab]], [[5n7t]], [[5mzk]], [[5mzi]], [[5mzc]], [[5fn0]] – PfKMO (mutant) + FAD + inhibitor<br />
 
- 
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*'''Phenol 2-monooxygenase (PMO)'''
 
- 
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**[[1foh]] – TcPMO + FAD – ''Trichosporon cutaneum''<br />
 
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**[[1pn0]] – TcPMO + FAD + phenol<br />
 
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*'''Phenylalanine 2-monooxygenase'''
 
- 
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**[[5pah]], [[6pah]] – hFMO catalytic domain + inhibitor <br />
 
- 
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*Phenylalanine 4-monooxygenase or phenylalanine-4-hydroxylase
 
- 
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See [[Hydroxylase]]
 
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*'''ActVA-Orf6 monooxygenase (AOMO)'''
 
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**[[1lq9]] – ScAOMO – ''Streptomyces coelicolor''<br />
 
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**[[1n5q]] – ScAOMO + sancycline <br />
 
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**[[1n5s]], [[1n5t]] – ScAOMO + acetyl dithranol<br />
 
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**[[1n5v]] – ScAOMO + nanaomycine <br />
 
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*Baeyer-Villiger monooxygenase (BVMO)
 
- 
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**[[6jdk]] – BVMO – ''Parvibaculum lavamentivorans''<br />
 
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*'''Flavin-containing monooxygenase'''
 
- 
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**[[2gv8]] – fyMO + FAD + NADP – fission yeast<br />
 
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**[[2gvc]] – fyMO + FAD + NADP + methimazole<br />
 
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**[[4a9w]] – SmMO + FAD – ''Stenotrophomonas maltophilia''<br />
 
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**[[4c5o]] – SmMO (mutant) + FAD <br />
 
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**[[5wan]] – EcMO + FMN + uracil – Escherichia coli<br />
 
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**[[5iq4]], [[5iq1]], [[5ipy]] – RnMO (mutant) + FAD + NAP – ''Roseovarius nubinhibens'' <br />
 
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**[[5gsn]] – RnMO (mutant) + FAD + NAP + methimazole <br />
 
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**[[4usr]] – PsMO + FAD <br />
 
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**[[3rp6]] – KpMO + FAD – ''Klebsiella pneumoniae''<br />
 
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**[[3rp8]] – KpMO (mutant) + FAD <br />
 
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**[[3rp7]] – KpMO + FAD + uric acid<br />
 
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**[[3c96]], [[2rgj]] – PaMO + FAD – ''Pseudomonas aeruginosa''<br />
 
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**[[2xvf]], [[2xve]] – MaMO + FAD – ''Methylophaga aminisulfidivorans'' <br />
 
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**[[2xvj]] – MaMO (mutant) + FAD + indole <br />
 
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**[[2xvi]] – MaMO (mutant) + FAD + O2<br />
 
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**[[2vqb]] – MaMO (mutant) + FAD + NADP + O2<br />
 
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**[[2xvh]], [[2xlu]], [[2xlt]] – MaMO + FAD + NADP derivative<br />
 
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**[[2xls]], [[2xlr]], [[2xlp]], [[2vq7]] – MaMO (mutant) + FAD + NADP <br />
 
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**[[5nmw]] – ZvMO + FAD – ''Zonocerus variegatus''<br />
 
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**[[5nmx]] – ZvMO + FAD + NADP <br />
 
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*2,4,6-trichlorophenol 4-monooxygenase
 
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**[[4g5e]] – MO – ''Cupriavidus necator''<br />
 
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*Chlorophenol 4-monooxygenase
 
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**[[4oo2]] – MO – ''Streptomyces globisporus''<br />
 
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**[[3k86]], [[3hwc]] – BcMO – ''Burkholderia cepacia'' <br />
 
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**[[3k87]] – BcMO + FAD <br />
 
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**[[3k88]] – BcMO + FAD + NAD <br />
 
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*Phenylacetone monooxygenase
 
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**[[4ovi]], [[4c74]] – TfMO + FAD + APADP – ''Thermobifida fusca''<br />
 
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**[[1w4x]] – TfMO + FAD<br />
 
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**[[2ylt]], [[2yls]], [[2ylr]] – TfMO + FAD + NADP <br />
 
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**[[2ylz]] – TfMO (mutant) + FAD <br />
 
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**[[4c77]] – TfMO (mutant) + FAD + APADP <br />
 
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**[[4d04]] – TfMO (mutant) + FAD + NAP <br />
 
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**[[4d03]], [[2ym2]], [[2ylx]], [[2ylw]] – TfMO (mutant) + FAD + NADP <br />
 
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**[[2ym1]] – TfMO (mutant) + FAD + NADP + O2<br />
 
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*6-hydroxynicotinate 3-monooxygenase
 
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**[[5eow]] – PpMO + FAD – ''Pseudomonas putida''<br />
 
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*Styrene monooxygenase
 
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**[[3ihm]] – PpMO <br />
 
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**[[4f07]] – PpMO (mutant) + FAD <br />
 
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*Tryptophan 2-monooxygenase
 
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**[[4iv9]] – MO + FAD – ''Pseudomonas savastanoi''<br />
 
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*Tryptophan 5-monooxygenase
 
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**[[1mlw]] – hMO + Fe + dihydrobiopterin <br />
 
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*Tyrosine 3-monooxygenase
 
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**[[2xsn]] – hMO + Zn<br />
 
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**[[2toh]] – rMO + Fe + dihydrobiopterin + tyrosine - rat<br />
 
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**[[2mda]] – rMO regulatory domain <br />
 
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*Nitronate monooxygenase
 
- 
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**[[4q4k]] – PaMO + FMN <br />
 
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**[[6e2a]] – PaMO + FMN + NAD<br />
 
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**[[5lsm]] – MO + FMN – ''Shewanella oneidensis''<br />
 
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**[[6bka]] – MO + FMN – ''Cyberlyndnera mrakii''<br />
 
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*2-hydroxbiphenyl 3-monooxygenase
 
- 
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**[[4z2r]] – PnMO + FAD – ''Pseudomonas nitroreducens''<br />
 
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**[[4cy6]] – PnMO (mutant) <br />
 
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**[[4z2u]], [[4z2t]], [[4cy8]] – PnMO (mutant) + FAD <br />
 
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**[[5brt]] – PnMO + FAD + hydroxybephenyl <br />
 
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*4-hydroxyphenylacetate 3-monooxygenase
 
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**[[4ira]] – BmMO + FAD – ''Brucella melitensis''<br />
 
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**[[3cb0]] – BmMO + FMN<br />
 
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**[[6eb0]] – EcMO oxygenase subunit<br />
 
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**[[6b1b]] – EcMO oxygenase subunit (mutant)<br />
 
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*Ornithine N(5)-monooxygenase
 
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**[[5cku]] – MO + FAD + NADP + ornithine – ''Neosartorya fumigata''<br />
 
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**[[4nzh]], [[4b69]] – AfMO + FAD + ornithine – ''Aspergillus fumigatus''<br />
 
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**[[4b65]] – AfMO + FAD + NADP <br />
 
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**[[4b68]], [[4b66]] – AfMO + FAD + NAP + arginine <br />
 
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**[[4b67]], [[4b63]] – AfMO + FAD + NADP + ornithine <br />
 
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**[[4b64]] – AfMO + FAD + NADP + lysine <br />
 
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**[[3s61]] – PaMO + FAD + NADP + ornithine derivative<br />
 
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*Steroid monooxygenase
 
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**[[4ap1]], [[4aos]] – RrMO + FAD + NADP – ''Rhodococcus rhodochrous''<br />
 
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**[[4aox]] – RrMO (mutant) + FAD <br />
 
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**[[4ap3]] – RrMO (mutant) + FAD + NADP <br />
 
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*Cyclohexanone monooxygenase
 
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**[[5m10]] – TmMO + FAD + NAP + nicotinamide – ''Thermocripsum municipale''<br />
 
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**[[5m0z]] – TmMO + FAD + NADP derivative <br />
 
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**[[6gqi]] – TmMO + FAD + NADP + hexanic acid <br />
 
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**[[6era]], [[6er9]] – RhMO + FAD + NADP – ''Rhodococcus''<br />
 
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**[[4rg4]], [[4rg3]], [[3gwf]], [[3gwd]] – RhMO + FAD + NAP + caprolactone <br />
 
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**[[3ucl]] – RhMO + FAD + NADP + cyclohexanone <br />
 
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*Lysine 6-monooxygenase
 
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**[[5cqf]] – MO – ''Pseudomonas syringae''<br />
 
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**[[4d7e]] – NfMO (mutant) + FAD – ''Nocardia farcinica''<br />
 
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**[[5o8p]] – EaMO + FAD – ''Erwinia amylovora''<br />
 
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**[[5o8r]] – EaMO + FAD + NADP <br />
 
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*EDTA monooxygenase
 
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**[[5dqp]] – MO – ''Chelativorans''<br />
 
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*Rifampicin monooxygenase or Pentachlorophenol 4-monooxygenase
 
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**[[5vqb]] – SvMO + FAD – ''Sterptomyces venezuelae''<br />
 
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**[[6brd]] – SvMO (mutant) + FAD + rifampicin <br />
 
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**[[5kow]] – NfMO + FAD <br />
 
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**[[5kox]] – NfMO + FAD + rifampicin <br />
 
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*3,6-diketocamphane 1,6 monooxygenase
 
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**[[5aec]] – PpMO <br />
 
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**[[4uwm]] – PpMO + FMN<br />
 
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*Lytic polysaccharide monooxygenase
 
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**[[5tki]], [[5foh]], [[4qi8]] – NcMO-2 + Cu – ''Neurospora crassa''''Italic text''<br />
 
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**[[5tkh]], [[5tkg]], [[5tkf]], [[4eir]] – NcMO-2 + Cu + O2 <br />
 
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**[[4eis]] – NcMO-3 + Cu + peroxide <br />
 
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**[[5iju]] – MO + Cu – ''Bacillus amyloliquefaciens''<br />
 
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**[[5acj]], [[5aci]], [[5ach]], [[5acg]], [[5acf]] – MO + Cu – ''Lentinus similis''<br />
 
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**[[4mai]] – moMO + Cu – mold<br />
 
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**[[4mah]] – moMO + Zn<br />
 
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**[[5no7]] – MO – ''Pycnoporus cinnabarinus''<br />
 
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*Peptidyl-glycine alpha-amidating monooxygenase
 
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**[[5mw0]], [[5wkw]] – rMO <br />
 
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**[[1yjl]] – rMO (mutant)<br />
 
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**[[3mib]], [[3mic]], [[3mid]], [[3mie]], [[3mif]], [[3mig]], [[3mih]], [[3mlj]], [[3mlk]], [[3mll]], [[1opm]] – rMO + Cu + Ni <br />
 
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**[[6ao6]], [[5wja]] – rMO (mutant) + Cu + Ni<br />
 
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**[[1sdw]] – rMO + Cu + Ni + O2 + threonine derivative<br />
 
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**[[1yjk]], [[1yip]], [[1phm]] – rMO + Cu<br />
 
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**[[1yi9]], [[6ay0]], [[6an3]], [[6amp]], [[6alv]], [[6ala]] – rMO (mutant) + Cu<br />
 
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**[[3fw0]] – rMO + Hg<br />
 
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**[[3fvz]] – rMO + Zn + Fe<br />
 
- 
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*Antibiotic biosynthesis monooxygenase
 
- 
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**[[4hl9]] – MO – ''Rhodospirillum rubrum''<br />
 
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**[[4dn9]] – MO – ''Chloroflexus aurantiacus''<br />
 
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**[[2ril]] – MO – ''Shewanella loihica''<br />
 
- 
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*Monooxygenase
 
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**[[2i7g]] – MO – ''Agrobacterium tumefaciens''<br />
 
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**[[5uq4]] – MtMO <br />
 
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**[[5f5l]] – MiMO – ''Micromonospora'' <br />
 
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**[[5f5n]] – MiMO + NAD + substrate <br />
 
- 
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*Monooxygenase TROPB
 
- 
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**[[6nes]] – TsMO + FAD – ''Talaromyces stipitatus''<br />
 
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**[[6nev]], [[6neu]] – TsMO (mutant) + FAD <br />
 
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**[[6net]] – TsMO + FAD + dihydroxy dimethylbenzaldehyde<br />
 
- 
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*Lactate 2-monooxygenase or lactate oxydase
 
- 
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**[[6dvi]] – MsLMO + FMN – ''Mycobacterium smegmatis''<br />
 
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**[[6dvh]] – MsLMO (mutant) + FMN <br />
 
- 
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*Squalene monooxygenase or squalene epoxidase
 
- 
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**[[6c6r]], [[6c6p]], [[6c6n]] – hSMO + FAD + inhibitor<br />
 
- 
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*Dimethyl-sulfide monooxygenase
 
- 
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**[[6ak1]] – DMOA – ''Hyphomicrobium sulfonivorans''<br />
 
- 
-
*Salicylate 1-monooxygenase or salicylate hydroxylase
 
- 
-
See [[Hydroxylase]]
 
- 
-
'''Methane monooxygenase''' See [[Methane monooxygenase]]
 
- 
-
'''Camphor 5-monooxygenase''' See [[Cytochrome P450]]
 
- 
-
'''Luciferin 4-monooxygenase and Alkanal monooxygenase''' See [[Luciferase]]
 
-
}}
 
== References ==
== References ==

Current revision

Glycosylated lytic polysaccharide monooxygenase complex with Cu(II) (orange) and peroxide (PDB code 5tkh)

Drag the structure with the mouse to rotate

References

  1. ↑ Sciara G, Kendrew SG, Miele AE, Marsh NG, Federici L, Malatesta F, Schimperna G, Savino C, Vallone B. The structure of ActVA-Orf6, a novel type of monooxygenase involved in actinorhodin biosynthesis. EMBO J. 2003 Jan 15;22(2):205-15. PMID:12514126 doi:http://dx.doi.org/10.1093/emboj/cdg031
  2. ↑ Fraaije MW, Wu J, Heuts DP, van Hellemond EW, Spelberg JH, Janssen DB. Discovery of a thermostable Baeyer-Villiger monooxygenase by genome mining. Appl Microbiol Biotechnol. 2005 Jan;66(4):393-400. PMID:15599520 doi:10.1007/s00253-004-1749-5
  3. ↑ Benitez AR, Tweedy S, Baker Dockrey SA, Lukowski AL, Wymore T, Khare D, Brooks CL 3rd, Palfey BA, Smith JL, Narayan ARH. Structural basis for selectivity in flavin-dependent monooxygenase-catalyzed oxidative dearomatization. ACS Catal. 2019 Apr 5;9(4):3633-3640. doi: 10.1021/acscatal.8b04575. Epub 2019, Mar 25. PMID:31346489 doi:http://dx.doi.org/10.1021/acscatal.8b04575
  4. ↑ Yang W, Moore IF, Koteva KP, Bareich DC, Hughes DW, Wright GD. TetX is a flavin-dependent monooxygenase conferring resistance to tetracycline antibiotics. J Biol Chem. 2004 Dec 10;279(50):52346-52. doi: 10.1074/jbc.M409573200. Epub 2004, Sep 27. PMID:15452119 doi:http://dx.doi.org/10.1074/jbc.M409573200
  5. ↑ Rudzka K, Moreno DM, Eipper B, Mains R, Estrin DA, Amzel LM. Coordination of peroxide to the Cu(M) center of peptidylglycine alpha-hydroxylating monooxygenase (PHM): structural and computational study. J Biol Inorg Chem. 2012 Dec 18. PMID:23247335 doi:10.1007/s00775-012-0967-z

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