Rhea - reaction knowledgebase

Enzymes

UniProtKB ^help_outline	3 proteins
Enzyme class ^help_outline	EC 1.14.14.52 (S)-limonene 7-monooxygenase
GO Molecular Function ^help_outline	GO:0018676 (S)-limonene 7-monooxygenase activity

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Name ^help_outline (4S)-limonene Identifier CHEBI:15383 (Beilstein: 2323991; CAS: 5989-54-8) ^help_outline Charge 0 Formula C10H16 InChIKey^help_outline XMGQYMWWDOXHJM-SNVBAGLBSA-N SMILES^help_outline [H][C@@]1(CCC(C)=CC1)C(C)=C 2D coordinates Mol file for the small molecule Search links Involved in 7 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline O₂ Identifier CHEBI:15379 (CAS: 7782-44-7) ^help_outline Charge 0 Formula O2 InChIKey^help_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILES^help_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,709 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name^help_outline reduced [NADPH—hemoprotein reductase] Identifier RHEA-COMP:11964 Reactive part ^help_outline
- Name ^help_outline FMNH₂ Identifier CHEBI:57618 (Beilstein: 6258176) ^help_outline Charge -2 Formula C17H21N4O9P InChIKey^help_outline YTNIXZGTHTVJBW-SCRDCRAPSA-L SMILES^help_outline Cc1cc2Nc3c([nH]c(=O)[nH]c3=O)N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])([O-])=O)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 794 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 734 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline (4S)-perillyl alcohol Identifier CHEBI:10782 (CAS: 536-59-4,18457-55-1) ^help_outline Charge 0 Formula C10H16O InChIKey^help_outline NDTYTMIUWGWIMO-SNVBAGLBSA-N SMILES^help_outline CC(=C)[C@H]1CCC(CO)=CC1 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H⁺ Identifier CHEBI:15378 Charge 1 Formula H InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,431 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H₂O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) ^help_outline Charge 0 Formula H2O InChIKey^help_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILES^help_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,204 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name^help_outline oxidized [NADPH—hemoprotein reductase] Identifier RHEA-COMP:11965 Reactive part ^help_outline
- Name ^help_outline FMN Identifier CHEBI:58210 Charge -3 Formula C17H18N4O9P InChIKey^help_outline ANKZYBDXHMZBDK-SCRDCRAPSA-K SMILES^help_outline C12=NC([N-]C(C1=NC=3C(N2C[C@@H]([C@@H]([C@@H](COP(=O)([O-])[O-])O)O)O)=CC(=C(C3)C)C)=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 804 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 734 reaction(s) Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:23432	RHEA:23433	RHEA:23434	RHEA:23435
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	3 proteins
EC numbers ^help_outline	1.14.14.52
Gene Ontology ^help_outline	GO:0018676
KEGG ^help_outline				R02470
MetaCyc ^help_outline		--LIMONENE-7-MONOOXYGENASE-RXN

Publications

Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves.

Karp F., Mihaliak C.A., Harris J.L., Croteau R.

Microsomal preparations from the epidermal oil glands of Mentha piperita, Mentha spicata, and Perilla frutescens leaves catalyze the NADPH- and O2-dependent allylic hydroxylation of the monoterpene olefin (-)-limonene at C-3, C-6, and C-7, respectively, to produce the corresponding alcohols, (-)-t ... >> More

Microsomal preparations from the epidermal oil glands of Mentha piperita, Mentha spicata, and Perilla frutescens leaves catalyze the NADPH- and O2-dependent allylic hydroxylation of the monoterpene olefin (-)-limonene at C-3, C-6, and C-7, respectively, to produce the corresponding alcohols, (-)-trans-isopiperitenol, (-)-trans-carveol, and (-)-perillyl alcohol. These transformations are the key steps in the biosynthesis of oxygenated monoterpenes in the respective species, and the responsible enzyme systems meet most of the established criteria for cytochrome P450-dependent mixed function oxygenases. The reactions catalyzed are completely regiospecific and, while exhibiting only a modest degree of enantioselectivity, are highly specific for limonene as substrate. Of numerous monoterpene olefins tested, including several positional isomers of limonene, only the 8,9-dihydro analog served as an alternate substrate for ring (C-3 and C-6) hydroxylation, but not side chain (C-7) hydroxylation. In addition to the regiospecificity of the allylic hydroxylation, these enzymes are also readily distinguishable based on differential inhibition by substituted imidazoles. << Less

Arch Biochem Biophys 276:219-226(1990) [PubMed] [EuropePMC]

This publication is cited by 2 other entries.

RHEA:23432 (4S)-limonene + O2 + reduced [NADPH--hemoprotein reductase] = (4S)-perillyl alcohol + H(+) + H2O + oxidized [NADPH--hemoprotein reductase]

Enzymes

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Cross-references

Publications

Monoterpene biosynthesis: specificity of the hydroxylations of (-)-limonene by enzyme preparations from peppermint (Mentha piperita), spearmint (Mentha spicata), and perilla (Perilla frutescens) leaves.