Trihydroxypterocarpan dimethylallyltransferase

Trihydroxypterocarpan dimethylallyltransferase
Identifiers
EC no.2.5.1.36
CAS no.70851-94-4
Databases
BRENDAenzyme data
ExPASyNiceZyme view
KEGGenzyme entry
MetaCycmetabolic pathway
Rheareactions
PDB structuresRCSB PDB PDBe PDBsum
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Trihydroxypterocarpan dimethylallyltransferase (EC 2.5.1.36, dimethylallylpyrophosphate:3,6a,9-trihydroxypterocarpan dimethylallyltransferase, dimethylallylpyrophosphate:trihydroxypterocarpan dimethylallyl transferase, dimethylallyl-diphosphate:(6aS,11aS)-3,6a,9-trihydroxypterocarpan dimethyltransferase) is an enzyme with systematic name dimethylallyl-diphosphate:(6aS,11aS)-3,6a,9-trihydroxypterocarpan dimethylallyltransferase.[1] It catalyses two related chemical reactions in which an prenyl unit is added to a phenyl ring. The enzyme uses dimethylallyl pyrophosphate to provide the five-carbon fragment, with pyrophosphate (PPi) as a byproduct:[2]

+
 
 
 
PPi
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27121915.
glyceocarpin

The enzyme can also catalyse the addition of the prenyl group at the alternative position next to the oxygen of the dihydropyran ring, giving 4-dimethylallylglycinol.

2D representation of the chemical structure of glycinol (pterocarpan).
glycinol
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PPi
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27121834.
4-dimethylallylglycinol

These compounds are intermediates in glyceollin biosynthesis in soybean.[3] The final step is catalysed by the enzyme glyceollin synthase.[4]

References

  1. ↑ Leube J, Grisebach H (1983). "Further studies on induction of enzymes of phytoalexin synthesis in soybean and cultured soybean cells". Z. Naturforsch. C: Biosci. 38 (9–10): 730–735. doi:10.1515/znc-1983-9-1011.
  2. ↑ Enzyme 2.5.1.36 at KEGG Pathway Database.
  3. ↑ Zähringer U, Schaller E, Grisebach H (1981). "Induction of phytoalexin synthesis in soybean. Structure and reactions of naturally occurring and enzymatically prepared prenylated pterocarpans from elicitor-treated cotyledons and cell cultures of soybean". Z. Naturforsch. C. 36 (3–4): 234–241. doi:10.1515/znc-1981-3-409.
  4. ↑ Welle R, Grisebach H (1988). "Induction of phytoalexin synthesis in soybean: enzymatic cyclization of prenylated pterocarpans to glyceollin isomers". Arch. Biochem. Biophys. 263 (1): 191–8. doi:10.1016/0003-9861(88)90627-3. PMID 3369863.