Abstract
Two dimethylallyltryptophan synthases, FgaPT2 and 7-DMATS, which catalysed the prenylation of l-tryptophan at positions C4 and C7, respectively, have been recently identified in Aspergillus fumigatus and proven biochemically. These enzymes were successfully used for the production of monoprenylated indole derivatives. In this study, we showed that C4,C7-diprenylated indole derivatives, e.g. 4,7-di-(dimethylallyl)-l-tryptophan, 4,7-di-(dimethylallyl)-l-abrine and 4,7-di-(dimethylallyl)-11-methyltryptophan, could be conveniently produced by tandem incubation of both enzymes. The structures of the isolated enzymatic products were elucidated by NMR and MS analyses. High conversion yields of up to 93% were achieved by an incubation sequence of FgaPT2 followed by 7-DMATS. The results reported in this study demonstrated the potential of secondary metabolite enzymes as promising tools for the production of designed compounds.
Abbreviations
- DMA:
-
Dimethylallyl
- DMAPP:
-
Dimethylallyl diphosphate
- DMAT:
-
Dimethylallyltryptophan
- DMATS:
-
Dimethylallyltryptophan synthase
References
Botta B, Monache GD, Menendez P et al (2005) Novel prenyltransferase enzymes as a tool for flavonoid prenylation. Trends Pharmacol Sci 26:606–608
Koeller KM, Wong CH (2001) Enzymes for chemical synthesis. Nature 409:232–240
Kremer A, Li S-M (2008) Potential of a 7-dimethylallyltryptophan synthase as a tool for production of prenylated indole derivatives. Appl Microbiol Biotechnol 79:951–961
Kremer A, Westrich L, Li S-M (2007) A 7-dimethylallyltryptophan synthase from Aspergillus fumigatus: overproduction, purification and biochemical characterization. Microbiology 153:3409–3416
Steffan N, Unsöld IA, Li S-M (2007) Chemoenzymatic synthesis of prenylated indole derivatives by using a 4-dimethylallyltryptophan synthase from Aspergillus fumigatus. Chembiochem 8:1298–1307
Steffan N, Grundmann A, Yin W-B et al (2009) Indole prenyltransferases from fungi: a new enzyme group with high potential for the production of prenylated indole derivatives. Curr Med Chem 16:218–231
Unsöld IA, Li S-M (2005) Overproduction, purification and characterization of FgaPT2, a dimethylallyltryptophan synthase from Aspergillus fumigatus. Microbiology 151:1499–1505
Acknowledgments
This work was supported by the Deutsche Forschungsgesellschaft and the Deutscher Akademischer Austauschdienst (DAAD) (PPP programme) (to S.-M. Li). H.-L. Ruan was a recipient of a fellowship from China Scholarship Council.
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Communicated by Axel Brakhage.
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Ruan, HL., Stec, E. & Li, SM. Production of diprenylated indole derivatives by tandem incubation of two recombinant dimethylallyltryptophan synthases. Arch Microbiol 191, 791–795 (2009). https://doi.org/10.1007/s00203-009-0504-9
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DOI: https://doi.org/10.1007/s00203-009-0504-9