IUBMB Enzyme Nomenclature

EC 2.5.1.106

Accepted name: tryprostatin B synthase

Reaction: dimethylallyl diphosphate + brevianamide F = diphosphate + tryprostatin B

For diagram of reaction click here.

Glossary: brevianamide F = (3S,8aS)-3-(1H-indol-3-ylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
tryprostatin B = (3S,8aS)-3-{[2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Other name(s): ftmPT1 (gene name); brevianamide F prenyltransferase (ambiguous)

Systematic name: dimethylallyl-diphosphate:brevianamide-F dimethylallyl-C-2-transferase

Comments: The enzyme from the fungus Aspergillus fumigatus can also prenylate other tryptophan-containing cyclic dipeptides. Prenylation occurs mainly at C-2 [1], but also at C-3 [2]. Involved in the biosynthetic pathways of several indole alkaloids such as tryprostatins, cyclotryprostatins, spirotryprostatins, fumitremorgins and verruculogen.

Links to other databases: BRENDA, EXPASY, GTD, KEGG, CAS registry number:

References:

1. Grundmann, A. and Li, S.M. Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus. Microbiology 151 (2005) 2199-2207. [PMID: 16000710]

2. Wollinsky, B., Ludwig, L., Xie, X. and Li, S.M. Breaking the regioselectivity of indole prenyltransferases: identification of regular C3-prenylated hexahydropyrrolo[2,3-b]indoles as side products of the regular C2-prenyltransferase FtmPT1. Org. Biomol. Chem. 10 (2012) 9262-9270. [PMID: 23090579]

[EC 2.5.1.106 created 2013]


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