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Entry
EC 2.5.1.67                 Enzyme                                 

Name
chrysanthemyl diphosphate synthase;
CPPase
Class
Transferases;
Transferring alkyl or aryl groups, other than methyl groups;
Transferring alkyl or aryl groups, other than methyl groups (only sub-subclass identified to date)
BRITE hierarchy
Sysname
dimethylallyl-diphosphate:dimethylallyl-diphosphate dimethylallyltransferase (chrysanthemyl-diphosphate-forming)
Reaction(IUBMB)
2 dimethylallyl diphosphate = diphosphate + chrysanthemyl diphosphate [RN:R08948]
Reaction(KEGG)
Substrate
dimethylallyl diphosphate [CPD:C00235]
Product
diphosphate [CPD:C00013];
chrysanthemyl diphosphate [CPD:C18051]
Comment
Requires a divalent metal ion for activity, with Mg2+ being better than Mn2+ [1]. Chrysanthemyl diphosphate is a monoterpene with a non-head-to-tail linkage. It is unlike most monoterpenoids, which are derived from geranyl diphosphate and have isoprene units that are linked head-to-tail. The mechanism of its formation is similar to that of the early steps of {terp/squalphyto::squalene and phytoene biosynthesis}. Chrysanthemyl diphosphate is the precursor of chrysanthemic acid, the acid half of the pyrethroid insecticides found in chrysanthemums.
History
EC 2.5.1.67 created 2007
Reference
1  [PMID:11287653]
  Authors
Rivera SB, Swedlund BD, King GJ, Bell RN, Hussey CE Jr, Shattuck-Eidens DM, Wrobel WM, Peiser GD, Poulter CD.
  Title
Chrysanthemyl diphosphate synthase: isolation of the gene and characterization of the recombinant non-head-to-tail monoterpene synthase from Chrysanthemum cinerariaefolium.
  Journal
Proc Natl Acad Sci U S A 98:4373-8 (2001)
DOI:10.1073/pnas.071543598
Reference
2  [PMID:12783539]
  Authors
Erickson HK, Poulter CD.
  Title
Chrysanthemyl diphosphate synthase. The relationship among chain elongation, branching, and cyclopropanation reactions in the isoprenoid biosynthetic pathway.
  Journal
J Am Chem Soc 125:6886-8 (2003)
DOI:10.1021/ja034520g
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 2.5.1.67
IUBMB Enzyme Nomenclature: 2.5.1.67
ExPASy - ENZYME nomenclature database: 2.5.1.67
BRENDA, the Enzyme Database: 2.5.1.67

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