KEGG   ENZYME: 2.5.1.106
Entry
EC 2.5.1.106                Enzyme                                 

Name
tryprostatin B synthase;
ftmPT1 (gene name);
brevianamide F prenyltransferase (ambiguous)
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)
Sysname
dimethylallyl-diphosphate:brevianamide-F dimethylallyl-C-2-transferase
Reaction(IUBMB)
dimethylallyl diphosphate + brevianamide F = diphosphate + tryprostatin B [RN:R10340]
Reaction(KEGG)
R10340
Substrate
dimethylallyl diphosphate [CPD:C00235];
brevianamide F [CPD:C20563]
Product
diphosphate [CPD:C00013];
tryprostatin B [CPD:C20512]
Comment
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.
History
EC 2.5.1.106 created 2013
Pathway
ec00404  Staurosporine biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K14132  tryprostatin B synthase
Genes
AFM: AFUA_8G00210
NFI: NFIA_093720
Reference
1  [PMID:16000710]
  Authors
Grundmann A, Li SM
  Title
Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus.
  Journal
Microbiology 151:2199-207 (2005)
DOI:10.1099/mic.0.27962-0
  Sequence
Reference
2  [PMID:23090579]
  Authors
Wollinsky B, Ludwig L, Xie X, Li SM
  Title
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.
  Journal
Org Biomol Chem 10:9262-70 (2012)
DOI:10.1039/c2ob26149a
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 2.5.1.106
IUBMB Enzyme Nomenclature: 2.5.1.106
ExPASy - ENZYME nomenclature database: 2.5.1.106
BRENDA, the Enzyme Database: 2.5.1.106

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