8-hydroxyfuranocoumarin 8-O-methyltransferase

8-hydroxyfuranocoumarin 8-O-methyltransferase
Identifiers
EC no.2.1.1.70
CAS no.67339-13-3
Databases
BRENDAenzyme data
ExPASyNiceZyme view
KEGGenzyme entry
MetaCycmetabolic pathway
Rheareactions
PDB structuresRCSB PDB PDBe PDBsum
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NCBIproteins

8-hydroxyfuranocoumarin 8-O-methyltransferase (EC 2.1.1.70, furanocoumarin 8-methyltransferase, furanocoumarin 8-O-methyl-transferase, xanthotoxol 8-O-methyltransferase, XMT, SAM:xanthotoxol O-methyltransferase, S-adenosyl-L-methionine:8-hydroxyfuranocoumarin 8-O-methyltransferase, xanthotoxol methyltransferase, xanthotoxol O-methyltransferase, S-adenosyl-L-methionine:xanthotoxol O-methyltransferase, S-adenosyl-L-methionine-xanthotoxol O-methyltransferase) is an enzyme with systematic name S-adenosyl-L-methionine:8-hydroxyfurocoumarin 8-O-methyltransferase.[1][2][3] This enzyme catalyses the following general chemical reaction

S-adenosyl-L-methionine + an 8-hydroxyfurocoumarin S-adenosyl-L-homocysteine + an 8-methoxyfurocoumarin (general reaction)

For example, xanthotoxol is converted to methoxsalen:[4][5]

+ SAM
 
 
 
 
Rightward reaction arrow
 
 
 
+ SAH
 

These are methylation reaction in which the methyl group comes from the cofactor, S-adenosyl methionine (SAM), which becomes S-adenosyl-L-homocysteine (SAH).

References

  1. ↑ Thompson HJ, Sharma SK, Brown SA (June 1978). "O-methyltransferases of furanocoumarin biosynthesis". Archives of Biochemistry and Biophysics. 188 (2): 272–81. doi:10.1016/s0003-9861(78)80009-5. PMID 28084.
  2. ↑ Sharma SK, Garrett JM, Brown SA (1979). "Separation of the S-adenosylmethionine: 5- and 8-hydroxyfuranocoumarin O-methyltransferases of Ruta graveolens L. by general ligand affinity chromatography". Zeitschrift für Naturforschung C. 34 (5–6): 387–91. doi:10.1515/znc-1979-5-611. PMID 156999.
  3. ↑ Hehmann M, Lukacin R, Ekiert H, Matern U (March 2004). "Furanocoumarin biosynthesis in Ammi majus L. Cloning of bergaptol O-methyltransferase". European Journal of Biochemistry. 271 (5): 932–40. doi:10.1111/j.1432-1033.2004.03995.x. PMID 15009205.
  4. ↑ Hauffe, K.D.; Hahlbrock, K.; Scheel, D. (1986). "Elicitor-stimulated furanocoumarin biosynthesis in cultured parsley cells - S-adenosyl-L-methionine-bergaptol and S-adenosyl-L-methionine-xanthotoxol O-methyltransferases". Zeitschrift für Naturforschung C. 41: 228–239. doi:10.1515/znc-1986-1-234.
  5. ↑ Dewick PM (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). John Wiley & Sons. pp. 161, 164–165.