EC 2.1.1.69 - 5-hydroxyfuranocoumarin 5-O-methyltransferase

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IntEnz Enzyme Nomenclature
EC 2.1.1.69

Names

Accepted name:
5-hydroxyfuranocoumarin 5-O-methyltransferase
Other names:
furanocoumarin 5-O-methyltransferase
furanocoumarin 5-methyltransferase
bergaptol 5-O-methyltransferase
bergaptol O-methyltransferase
bergaptol methyltransferase
S-adenosyl-L-methionine:bergaptolO-methyltransferase
BMT
S-adenosyl-L-methionine:5-hydroxyfuranocoumarin 5-O-methyltransferase
Systematic name:
S-adenosyl-L-methionine:5-hydroxyfurocoumarin 5-O-methyltransferase

Reactions

Comments:

Converts bergaptol into bergapten, which has therapeutic potential in the treatment of psoriasis as it has photosensitizing and antiproliferative activities [4]. The enzyme methylates the 5-hydroxy group of some hydroxy- and methylcoumarins, such as 5-hydroxyxanthotoxin, but has little activity on non-coumarin phenols [1]. Caffeate, 5-hydroxyferulate and daphnetin are not substrates [4]. Cu2+, Zn2+ and Co2+ cause enzyme inhibition [4]. (see also EC 2.1.1.70, 8-hydroxyfuranocoumarin 8-O-methyltransferase).

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , DIAGRAM , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Structural data: CSA , EC2PDB
Gene Ontology: GO:0030752
CAS Registry Number: 67339-12-2
UniProtKB/Swiss-Prot:

References

  1. Thompson, H.J., Sharma, S.K. and Brown, S.A.
    O-Methyltransferases of furanocoumarin biosynthesis.
    Arch. Biochem. Biophys. 188: 272-281 (1978). [PMID: 28084]
  2. Sharma, S.K., Garrett, J.M. and Brown, S.A.
    Separation of the S-adenosylmethionine: 5- and 8-hydroxyfuranocoumarin O-methyltransferases of Ruta graveolens L. by general ligand affinity chromatography.
    Z. Naturforsch. C: Biosci. 34: 387-391 (1979). [PMID: 156999]
  3. Hauffe, K.D., Hahlbrock, K. and Scheel, D.
    Elicitor-stimulated furanocoumarin biosynthesis in cultured parsley cells — S-adenosyl-L-methionine-bergaptol and S-adenosyl-L-methionine-xanthotoxol O-methyltransferases.
    Z. Naturforsch. C: Biosci. 41: 228-239 (1986).
  4. Hehmann, M., Lukačin, R., Ekiert, H. and Matern, U.
    Furanocoumarin biosynthesis in Ammi majus L. Cloning of bergaptol O-methyltransferase.
    Eur. J. Biochem. 271: 932-940 (2004). [PMID: 15009205]

[EC 2.1.1.69 created 1984 (EC 2.1.1.92 created 1989, incorporated 2006), modified 2006]