MMKMO_RHOER
ID MMKMO_RHOER Reviewed; 31 AA.
AC P82679;
DT 10-MAY-2004, integrated into UniProtKB/Swiss-Prot.
DT 01-OCT-2000, sequence version 1.
DT 03-AUG-2022, entry version 37.
DE RecName: Full=Monocyclic monoterpene ketone monooxygenase {ECO:0000303|PubMed:10769172};
DE Short=MMKMO {ECO:0000303|PubMed:10769172};
DE EC=1.14.13.105 {ECO:0000269|PubMed:10769172};
DE AltName: Full=Baeyer-Villiger monooxygenase {ECO:0000303|PubMed:10769172};
DE Short=BVMO {ECO:0000303|PubMed:10769172};
DE Flags: Fragment;
OS Rhodococcus erythropolis (Arthrobacter picolinophilus).
OC Bacteria; Actinobacteria; Corynebacteriales; Nocardiaceae; Rhodococcus;
OC Rhodococcus erythropolis group.
OX NCBI_TaxID=1833;
RN [1]
RP PROTEIN SEQUENCE, FUNCTION, CATALYTIC ACTIVITY, COFACTOR,
RP BIOPHYSICOCHEMICAL PROPERTIES, SUBUNIT, AND INDUCTION.
RC STRAIN=DCL 14;
RX PubMed=10769172; DOI=10.1042/0264-6021:3470693;
RA van der Werf M.J.;
RT "Purification and characterization of a Baeyer-Villiger mono-oxygenase from
RT Rhodococcus erythropolis DCL14 involved in three different monocyclic
RT monoterpene degradation pathways.";
RL Biochem. J. 347:693-701(2000).
CC -!- FUNCTION: Catalyzes the NADPH- and oxygen-dependent oxidation of the
CC monocyclic monoterpene ketones 1-hydroxy-2-oxolimonene, dihydrocarvone
CC and menthone. Is able to convert all enantiomers of these natural
CC substrates with almost equal efficiency. Is thus involved in the
CC conversion of the monocyclic monoterpene ketone intermediates formed in
CC the degradation pathways of all stereoisomers of three different
CC monocyclic monoterpenes, i.e. limonene, (dihydro)carveol and menthol,
CC which likely make R.erythropolis able to grow on these compounds as the
CC sole source of carbon and energy. {ECO:0000269|PubMed:10769172}.
CC -!- CATALYTIC ACTIVITY:
CC Reaction=1-hydroxylimonen-2-one + NADPH + O2 = 3-isopropenyl-6-
CC oxoheptanoate + H2O + NADP(+); Xref=Rhea:RHEA:55004,
CC ChEBI:CHEBI:15377, ChEBI:CHEBI:15379, ChEBI:CHEBI:50246,
CC ChEBI:CHEBI:57783, ChEBI:CHEBI:58349, ChEBI:CHEBI:64234;
CC EC=1.14.13.105; Evidence={ECO:0000269|PubMed:10769172};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:55005;
CC Evidence={ECO:0000305|PubMed:10769172};
CC -!- CATALYTIC ACTIVITY:
CC Reaction=(1R,4S)-1-hydroxylimonen-2-one + H(+) + NADPH + O2 = (4S,7S)-
CC 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + H2O + NADP(+);
CC Xref=Rhea:RHEA:53412, ChEBI:CHEBI:15377, ChEBI:CHEBI:15378,
CC ChEBI:CHEBI:15379, ChEBI:CHEBI:50245, ChEBI:CHEBI:57783,
CC ChEBI:CHEBI:58349, ChEBI:CHEBI:138596; EC=1.14.13.105;
CC Evidence={ECO:0000269|PubMed:10769172};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:53413;
CC Evidence={ECO:0000305|PubMed:10769172};
CC -!- CATALYTIC ACTIVITY:
CC Reaction=(1S,4R)-1-hydroxylimonen-2-one + H(+) + NADPH + O2 = (4R,7R)-
CC 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one + H2O + NADP(+);
CC Xref=Rhea:RHEA:53408, ChEBI:CHEBI:15377, ChEBI:CHEBI:15378,
CC ChEBI:CHEBI:15379, ChEBI:CHEBI:38249, ChEBI:CHEBI:57783,
CC ChEBI:CHEBI:58349, ChEBI:CHEBI:138597; EC=1.14.13.105;
CC Evidence={ECO:0000269|PubMed:10769172};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:53409;
CC Evidence={ECO:0000305|PubMed:10769172};
CC -!- CATALYTIC ACTIVITY:
CC Reaction=(1R,4R)-dihydrocarvone + H(+) + NADPH + O2 = (4R,7R)-4-
CC isopropenyl-7-methyloxepan-2-one + H2O + NADP(+);
CC Xref=Rhea:RHEA:52824, ChEBI:CHEBI:154, ChEBI:CHEBI:228,
CC ChEBI:CHEBI:15377, ChEBI:CHEBI:15378, ChEBI:CHEBI:15379,
CC ChEBI:CHEBI:57783, ChEBI:CHEBI:58349; EC=1.14.13.105;
CC Evidence={ECO:0000269|PubMed:10769172};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:52825;
CC Evidence={ECO:0000305|PubMed:10769172};
CC -!- CATALYTIC ACTIVITY:
CC Reaction=(1S,4R)-menthone + H(+) + NADPH + O2 = (4S,7R)-7-isopropyl-4-
CC methyloxepan-2-one + H2O + NADP(+); Xref=Rhea:RHEA:54872,
CC ChEBI:CHEBI:31, ChEBI:CHEBI:15377, ChEBI:CHEBI:15378,
CC ChEBI:CHEBI:15379, ChEBI:CHEBI:57783, ChEBI:CHEBI:58349,
CC ChEBI:CHEBI:138383; Evidence={ECO:0000269|PubMed:10769172};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:54873;
CC Evidence={ECO:0000305|PubMed:10769172};
CC -!- CATALYTIC ACTIVITY:
CC Reaction=(1R,4S)-menthone + H(+) + NADPH + O2 = (4R,7S)-7-isopropyl-4-
CC methyloxepan-2-one + H2O + NADP(+); Xref=Rhea:RHEA:32431,
CC ChEBI:CHEBI:15377, ChEBI:CHEBI:15378, ChEBI:CHEBI:15379,
CC ChEBI:CHEBI:15410, ChEBI:CHEBI:50250, ChEBI:CHEBI:57783,
CC ChEBI:CHEBI:58349; EC=1.14.13.105;
CC Evidence={ECO:0000269|PubMed:10769172};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:32432;
CC Evidence={ECO:0000305|PubMed:10769172};
CC -!- CATALYTIC ACTIVITY:
CC Reaction=(1S,4R)-isodihydrocarvone + H(+) + NADPH + O2 = (3S,6R)-6-
CC isopropenyl-3-methyloxepan-2-one + H2O + NADP(+);
CC Xref=Rhea:RHEA:52828, ChEBI:CHEBI:166, ChEBI:CHEBI:15377,
CC ChEBI:CHEBI:15378, ChEBI:CHEBI:15379, ChEBI:CHEBI:57783,
CC ChEBI:CHEBI:58349, ChEBI:CHEBI:64232; EC=1.14.13.105;
CC Evidence={ECO:0000269|PubMed:10769172};
CC PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:52829;
CC Evidence={ECO:0000305|PubMed:10769172};
CC -!- COFACTOR:
CC Name=FAD; Xref=ChEBI:CHEBI:57692;
CC Evidence={ECO:0000269|PubMed:10769172};
CC -!- BIOPHYSICOCHEMICAL PROPERTIES:
CC Kinetic parameters:
CC KM=0.13 mM for (4R)-dihydrocarvone {ECO:0000269|PubMed:10769172};
CC KM=0.01 mM for (1R,4S)-1-hydroxy-2-oxolimonene
CC {ECO:0000269|PubMed:10769172};
CC KM=0.13 mM for (1S,4R)-1-hydroxy-2-oxolimonene
CC {ECO:0000269|PubMed:10769172};
CC KM=0.12 mM for (1R,4S)-menthone {ECO:0000269|PubMed:10769172};
CC KM=0.01 mM for (1S,4R)-menthone {ECO:0000269|PubMed:10769172};
CC KM=0.038 mM for NADPH {ECO:0000269|PubMed:10769172};
CC Note=kcat is 3.9 sec(-1) with (4R)-dihydrocarvone as substrate. kcat
CC is 4.9 sec(-1) with (1R,4S)-1-hydroxy-2-oxolimonene as substrate.
CC kcat is 3.9 sec(-1) with (1S,4R)-1-hydroxy-2-oxolimonene as
CC substrate. kcat is 3.6 sec(-1) with (1R,4S)-menthone as substrate.
CC kcat is 6.0 sec(-1) with (1S,4R)-menthone as substrate.
CC {ECO:0000269|PubMed:10769172};
CC pH dependence:
CC Optimum pH is 9.5. {ECO:0000269|PubMed:10769172};
CC Temperature dependence:
CC Optimum temperature is about 36 degrees Celsius.
CC {ECO:0000269|PubMed:10769172};
CC -!- PATHWAY: Terpene metabolism; monoterpene degradation.
CC {ECO:0000305|PubMed:10769172}.
CC -!- SUBUNIT: Monomer. {ECO:0000269|PubMed:10769172}.
CC -!- INDUCTION: Induced by growth on limonene, carveol, dihydrocarveol or
CC (1R,3R,4S)-menthol. {ECO:0000269|PubMed:10769172}.
CC -!- MISCELLANEOUS: The 7-hydroxy-4-isopropenyl-7-methyloxepan-2-one lactone
CC obtained from 1-hydroxylimonen-2-one is unstable and undergoes a
CC spontaneous rearrangement to 3-isopropenyl-6-oxoheptanoate.
CC {ECO:0000269|PubMed:10769172}.
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DR SwissLipids; SLP:000001722; -.
DR SABIO-RK; P82679; -.
DR UniPathway; UPA00137; -.
DR GO; GO:0004497; F:monooxygenase activity; IDA:UniProtKB.
PE 1: Evidence at protein level;
KW Direct protein sequencing; FAD; Flavoprotein; NADP; Oxidoreductase.
FT CHAIN 1..>31
FT /note="Monocyclic monoterpene ketone monooxygenase"
FT /id="PRO_0000065027"
FT BINDING 20..25
FT /ligand="FAD"
FT /ligand_id="ChEBI:CHEBI:57692"
FT UNSURE 8
FT /note="T or G"
FT NON_TER 31
SQ SEQUENCE 31 AA; 3277 MW; E4CCEEB23AE609E7 CRC64;
MQTIPSTTET AADFDAVIXG AGFXGLYALH R
