Rhea - reaction knowledgebase

Reaction participants Show >> << Hide

Name ^help_outline 1-deoxypentalenate Identifier CHEBI:68650 Charge -1 Formula C15H21O2 InChIKey^help_outline DCFDRCCHOOORSB-DSKWVYQCSA-M SMILES^help_outline [H][C@@]12CC(C)(C)C[C@@]11[C@H](C)CC[C@@]1([H])C(=C2)C([O-])=O 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 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 2[4Fe-4S]-[ferredoxin] Identifier RHEA-COMP:10002 Reactive part ^help_outline
- Name ^help_outline [4Fe-4S]¹⁺ cluster Identifier CHEBI:33723 Charge 1 Formula Fe4S4 InChIKey^help_outline ISVAEKDKOPJTJN-UHFFFAOYSA-N Position^help_outline 1 SMILES^help_outline [S]12[Fe]3[S]4[Fe]1[S]1[Fe]2[S]3[Fe+]41 2D coordinates Mol file for the small molecule Search links Involved in 25 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name ^help_outline [4Fe-4S]¹⁺ cluster Identifier CHEBI:33723 Charge 1 Formula Fe4S4 InChIKey^help_outline ISVAEKDKOPJTJN-UHFFFAOYSA-N Position^help_outline 2 SMILES^help_outline [S]12[Fe]3[S]4[Fe]1[S]1[Fe]2[S]3[Fe+]41 2D coordinates Mol file for the small molecule Search links Involved in 25 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 16 reaction(s) 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 2[4Fe-4S]-[ferredoxin] Identifier RHEA-COMP:10004 Reactive part ^help_outline
- Name ^help_outline [4Fe-4S]²⁺ cluster Identifier CHEBI:33722 Charge 2 Formula Fe4S4 InChIKey^help_outline YEAYMLBNRJYVPB-UHFFFAOYSA-N Position^help_outline 1 SMILES^help_outline [S]12[Fe]3[S]4[Fe]1[S]1[Fe+]2[S]3[Fe+]41 2D coordinates Mol file for the small molecule Search links Involved in 25 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name ^help_outline [4Fe-4S]²⁺ cluster Identifier CHEBI:33722 Charge 2 Formula Fe4S4 InChIKey^help_outline YEAYMLBNRJYVPB-UHFFFAOYSA-N Position^help_outline 2 SMILES^help_outline [S]12[Fe]3[S]4[Fe]1[S]1[Fe+]2[S]3[Fe+]41 2D coordinates Mol file for the small molecule Search links Involved in 25 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 16 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline pentalenate Identifier CHEBI:68649 Charge -1 Formula C15H21O3 InChIKey^help_outline WBLTVUMJMJIOGQ-YCGCYHNXSA-M SMILES^help_outline [H][C@@]12CC[C@@H](C)[C@@]11CC(C)(C)[C@H](O)[C@@]1([H])C=C2C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:34499	RHEA:34500	RHEA:34501	RHEA:34502
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	1 proteins
EC numbers ^help_outline	1.14.15.11
KEGG ^help_outline				R10158
MetaCyc ^help_outline		RXNMETA-12666

Publications

Pentalenic acid is a shunt metabolite in the biosynthesis of the pentalenolactone family of metabolites: hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV_7469) of Streptomyces avermitilis.

Takamatsu S., Xu L.H., Fushinobu S., Shoun H., Komatsu M., Cane D.E., Ikeda H.

Pentalenic acid (1) has been isolated from many Streptomyces sp. as a co-metabolite of the sesquiterpenoid antibiotic pentalenolactone and related natural products. We have previously reported the identification of a 13.4-kb gene cluster in the genome of Streptomyces avermitilis implicated in the ... >> More

Pentalenic acid (1) has been isolated from many Streptomyces sp. as a co-metabolite of the sesquiterpenoid antibiotic pentalenolactone and related natural products. We have previously reported the identification of a 13.4-kb gene cluster in the genome of Streptomyces avermitilis implicated in the biosynthesis of the pentalenolactone family of metabolites consisting of 13 open reading frames. Detailed molecular genetic and biochemical studies have revealed that at least seven genes are involved in the biosynthesis of the newly discovered metabolites, neopentalenoketolactone, but no gene specifically dedicated to the formation of pentalenic acid (1) was evident in the same gene cluster. The wild-type strain of S. avermitilis, as well as its derivatives, mainly produce pentalenic acid (1), together with neopentalenoketolactone (9). Disruption of the sav7469 gene encoding a cytochrome P450 (CYP105D7), members of which class are associated with the hydroxylation of many structurally different compounds, abolished the production of pentalenic acid (1). The sav7469-deletion mutant derived from SUKA11 carrying pKU462∷ptl-clusterΔptlH accumulated 1-deoxypentalenic acid (5), but not pentalenic acid (1). Reintroduction of an extra-copy of the sav7469 gene to SUKA11 Δsav7469 carrying pKU462∷ptl-clusterΔptlH restored the production of pentalenic acid (1). Recombinant CYP105D7 prepared from Escherichia coli catalyzed the oxidative conversion of 1-deoxypentalenic acid (5) to pentalenic acid (1) in the presence of the electron-transport partners, ferredoxin (Fdx) and Fdx reductase, both in vivo and in vitro. These results unambiguously demonstrate that CYP105D7 is responsible for the conversion of 1-deoxypentalenic acid (5) to pentalenic acid (1), a shunt product in the biosynthesis of the pentalenolactone family of metabolites. << Less

J. Antibiot. 64:65-71(2011) [PubMed] [EuropePMC]

RHEA:34501 H2O + oxidized 2[4Fe-4S]-[ferredoxin] + pentalenate => 1-deoxypentalenate + 2 H(+) + O2 + reduced 2[4Fe-4S]-[ferredoxin] Reaction with net flow from right to left. help_outline

Reaction participants Show >> << Hide

Cross-references

Publications

Pentalenic acid is a shunt metabolite in the biosynthesis of the pentalenolactone family of metabolites: hydroxylation of 1-deoxypentalenic acid mediated by CYP105D7 (SAV_7469) of Streptomyces avermitilis.

RHEA:34501 H2O + oxidized 2[4Fe-4S]-[ferredoxin] + pentalenate => 1-deoxypentalenate + 2 H(+) + O2 + reduced 2[4Fe-4S]-[ferredoxin] Reaction with net flow from right to left. ^help_outline