Enzymes
UniProtKB help_outline | 1 proteins |
Reaction participants Show >> << Hide
- Name help_outline (Z,S)-pyrethrolone Identifier CHEBI:39111 (Beilstein: 2555216) help_outline Charge 0 Formula C11H14O2 InChIKeyhelp_outline IVGYSSJKFLEVIX-LWTINBJPSA-N SMILEShelp_outline CC1=C(C\C=C/C=C)C(=O)C[C@@H]1O 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 (1R,3R)-chrysanthemoyl-CoA Identifier CHEBI:143950 Charge -4 Formula C31H46N7O17P3S InChIKeyhelp_outline IOIRXYHMXCHGNR-JRAGNYAJSA-J SMILEShelp_outline C1([C@@H]([C@H]1C=C(C)C)C(=O)SCCNC(CCNC(=O)[C@@H](C(COP(OP(OC[C@H]2O[C@@H](N3C4=C(C(=NC=N4)N)N=C3)[C@@H]([C@@H]2OP([O-])([O-])=O)O)(=O)[O-])(=O)[O-])(C)C)O)=O)(C)C 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline pyrethrin I Identifier CHEBI:27815 (Beilstein: 2004306; CAS: 121-21-1) help_outline Charge 0 Formula C21H28O3 InChIKeyhelp_outline ROVGZAWFACYCSP-VUMXUWRFSA-N SMILEShelp_outline CC(C)=C[C@@H]1[C@@H](C(=O)O[C@H]2CC(=O)C(C\C=C/C=C)=C2C)C1(C)C 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
- Name help_outline CoA Identifier CHEBI:57287 (Beilstein: 11604429) help_outline Charge -4 Formula C21H32N7O16P3S InChIKeyhelp_outline RGJOEKWQDUBAIZ-IBOSZNHHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCS 2D coordinates Mol file for the small molecule Search links Involved in 1,511 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:60744 | RHEA:60745 | RHEA:60746 | RHEA:60747 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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MetaCyc help_outline |
Publications
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Identification and characterization of a GDSL lipase-like protein that catalyzes the ester-forming reaction for pyrethrin biosynthesis in Tanacetum cinerariifolium- a new target for plant protection.
Kikuta Y., Ueda H., Takahashi M., Mitsumori T., Yamada G., Sakamori K., Takeda K., Furutani S., Nakayama K., Katsuda Y., Hatanaka A., Matsuda K.
Although natural insecticides pyrethrins produced by Tanacetum cinerariifolium are used worldwide to control insect pest species, little information is known of their biosynthesis. From the buds of T. cinerariifolium, we have purified a protein that is able to transfer the chrysanthemoyl group fro ... >> More
Although natural insecticides pyrethrins produced by Tanacetum cinerariifolium are used worldwide to control insect pest species, little information is known of their biosynthesis. From the buds of T. cinerariifolium, we have purified a protein that is able to transfer the chrysanthemoyl group from the coenzyme A (CoA) thioester to pyrethrolone to produce pyrethrin I and have isolated cDNAs that encode the enzyme. To our surprise, the active principle was not a member of a known acyltransferase family but a member of the GDSL lipase family. The recombinant enzyme (TcGLIP) was expressed in Escherichia coli and displayed the acyltransferase reaction with high substrate specificity, recognized the absolute configurations of three asymmetric carbons and also showed esterase activity. A S40A mutation in the Block I domain reduced both acyltransferase and esterase activities, which suggested an important role of this serine residue in these two activities. The signal peptide directed the localization of TcGLIP::enhanced green fluorescent protein (EGFP) fusion, as well as EGFP, to the extracellular space. High TcGLIP gene expression was observed in the leaves of mature plants and seedlings as well as in buds and flowers, a finding that was consistent with the pyrethrin I content in these parts. Expression was enhanced in response to wounding, which suggested that the enzyme plays a key role in the defense mechanism of T. cinerariifolium. << Less
Plant J. 71:183-193(2012) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.