Prenyltransferases of the dimethylallyltryptophan synthase superfamily

Methods in Enzymology

Volumn 516, Issue , 2012, Pages 259-278

  Yu, Xia ^a   Li, Shu Ming ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Ascomycetes; Chemoenzymatic synthesis; DMATS superfamily; Indole prenyltransferase; Secondary metabolite biosynthesis

Indexed keywords

COMPLEMENTARY DNA; DIMETHYLALLYLTRANSFERASE; DIPEPTIDE; GENOMIC DNA;

ARTICLE; BIODIVERSITY; BIOTECHNOLOGY; DNA ISOLATION; DNA SYNTHESIS; ENZYME ANALYSIS; ENZYME ASSAY; ENZYME KINETICS; ENZYME MECHANISM; ENZYME SUBSTRATE; ENZYME SYNTHESIS; ESCHERICHIA COLI; FUNGAL METABOLISM; FUNGUS CULTURE; FUNGUS SPORE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR CLONING; NONHUMAN; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; PROTEIN FAMILY; PROTEIN SYNTHESIS; RNA ISOLATION; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY;

ASCOMYCOTA;

EID: 84867031524     PISSN: 00766879     EISSN: 15577988     Source Type: Book Series    
DOI: 10.1016/B978-0-12-394291-3.00005-8     Document Type: Chapter

References (33)

1. Y. Ding, J.R. Wet, J. Cavalcoli, S. Li, T.J. Greshock, and K.A. Miller Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp Journal of the American Chemical Society 132 2010 12733 12740
2. Y. Ding, R.M. Williams, and D.H. Sherman Molecular analysis of a 4-dimethylallyltryptophan synthase from Malbranchea aurantiaca The Journal of Biological Chemistry 283 2008 16068 16076
3. A. Grundmann, T. Kuznetsova, S.S. Afiyatullov, and S.-M. Li FtmPT2, an N-prenyltransferase from Aspergillus fumigatus, catalyses the last step in the biosynthesis of fumitremorgin B Chembiochem 9 2008 2059 2063
4. A. Grundmann, and S.-M. Li Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus Microbiology 151 2005 2199 2207 (Pubitemid 40984293)
5. H.D. Jain, C. Zhang, S. Zhou, H. Zhou, J. Ma, and X. Liu Synthesis and structure-activity relationship studies on tryprostatin A, a potent inhibitor of breast cancer resistance protein Bioorganic & Medicinal Chemistry 16 2008 4626 4651 (Pubitemid 351539021)
6. M. Jost, G. Zocher, S. Tarcz, M. Matuschek, X. Xie, and S.-M. Li Structure-function analysis of an enzymatic prenyl transfer reaction identifies a reaction chamber with modifiable specificity Journal of the American Chemical Society 132 2010 17849 17858
7. A. Kremer, and S.-M. Li A tyrosine O-prenyltransferase catalyses the first pathway-specific step in the biosynthesis of sirodesmin PL Microbiology 156 2010 278 286
8. A. Kremer, L. Westrich, and S.-M. Li A 7-dimethylallyltryptophan synthase from Aspergillus fumigatus: Overproduction, purification and biochemical characterization Microbiology 153 2007 3409 3416 (Pubitemid 47629546)
9. S.-M. Li Applications of dimethylallyltryptophan synthases and other indole prenyltransferases for structural modification of natural products Applied Microbiology and Biotechnology 84 2009 631 639
10. S.-M. Li Evolution of aromatic prenyltransferases in the biosynthesis of indole derivatives Phytochemistry 70 2009 1746 1757
11. S.-M. Li Prenylated indole derivatives from fungi: Structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis Natural Product Reports 27 2010 57 78
12. X. Liu, and C.T. Walsh Characterization of cyclo-acetoacetyl-L-tryptophan dimethylallyltransferase in cyclopiazonic acid biosynthesis: Substrate promiscuity and site directed mutagenesis studies Biochemistry 48 2009 11032 11044
13. Y.P. Lu, H.G. Liu, and P.H. Liang Different reaction mechanisms for cis- and trans-prenyltransferases Biochemical and Biophysical Research Communications 379 2009 351 355
14. L.Y.P. Luk, and M.E. Tanner Mechanism of dimethylallyltryptophan synthase: Evidence for a dimethylallyl cation intermediate in an aromatic prenyltransferase reaction Journal of the American Chemical Society 131 2009 13932 13933
15. A. Markert, N. Steffan, K. Ploss, S. Hellwig, U. Steiner, and C. Drewke Biosynthesis and accumulation of ergoline alkaloids in a mutualistic association between Ipomoea asarifolia (Convolvulaceae) and a Clavicipitalean fungus Plant Physiology 147 2008 296 305 (Pubitemid 352844368)
16. U. Metzger, C. Schall, G. Zocher, I. Unsöld, E. Stec, and S.-M. Li The structure of dimethylallyl tryptophan synthase reveals a common architecture of aromatic prenyltransferases in fungi and bacteria Proceedings of the National Academy of Sciences of the United States of America 106 2009 14309 14314
17. J.F. Sanchez, R. Entwistle, J.H. Hung, J. Yaegashi, S. Jain, and Y.M. Chiang Genome-based deletion analysis reveals the prenyl xanthone biosynthesis pathway in Aspergillus nidulans Journal of the American Chemical Society 133 2011 4010 4017
18. P. Schneider, M. Weber, and D. Hoffmeister The Aspergillus nidulans enzyme TdiB catalyzes prenyltransfer to the precursor of bioactive asterriquinones Fungal Genetics and Biology 45 2008 302 309 (Pubitemid 351192336)
19. E. Stec, N. Steffan, A. Kremer, H. Zou, X. Zheng, and S.-M. Li Two lysine residues are responsible for the enzymatic activities of indole prenyltransferases from fungi Chembiochem 9 2008 2055 2058
20. N. Steffan, A. Grundmann, W.-B. Yin, A. Kremer, and S.-M. Li Indole prenyltransferases from fungi: A new enzyme group with high potential for the production of prenylated indole derivatives Current Medicinal Chemistry 16 2009 218 231
21. N. Steffan, I.A. Unsöld, and S.-M. Li Chemoenzymatic synthesis of prenylated indole derivatives by using a 4-dimethylallyltryptophan synthase from Aspergillus fumigatus Chembiochem 8 2007 1298 1307 (Pubitemid 47171997)
22. H.F. Tsai, H. Wang, J.C. Gebler, C.D. Poulter, and C.L. Schardl The Claviceps purpurea gene encoding dimethylallyltryptophan synthase, the committed step for ergot alkaloid biosynthesis Biochemical and Biophysical Research Communications 216 1995 119 125
23. I.A. Unsöld, and S.-M. Li Overproduction, purification and characterization of FgaPT2, a dimethylallyltryptophan synthase from Aspergillus fumigatus Microbiology 151 2005 1499 1505 (Pubitemid 40711797)
24. I.A. Unsöld, and S.-M. Li Reverse prenyltransferase in the biosynthesis of fumigaclavine C in Aspergillus fumigatus: Gene expression, purification and characterization of fumigaclavine C synthase FgaPT1 Chembiochem 7 2006 158 164 (Pubitemid 43076299)
25. K. Yazaki, K. Sasaki, and Y. Tsurumaru Prenylation of aromatic compounds, a key diversification of plant secondary metabolites Phytochemistry 70 2009 1739 1745
26. W.-B. Yin, A. Grundmann, J. Cheng, and S.-M. Li Acetylaszonalenin biosynthesis in Neosartorya fischeri: Identification of the biosynthetic gene cluster by genomic mining and functional proof of the genes by biochemical investigation The Journal of Biological Chemistry 284 2009 100 109
27. W.-B. Yin, H.-L. Ruan, L. Westrich, A. Grundmann, and S.-M. Li CdpNPT, an N-prenyltransferase from Aspergillus fumigatus: Overproduction, purification and biochemical characterisation Chembiochem 8 2007 1154 1161 (Pubitemid 47194823)
28. W.-B. Yin, X. Yu, X.-L. Xie, and S.-M. Li Preparation of pyrrolo[2,3-b]indoles carrying a ß-configured reverse C3-dimethylallyl moiety by using a recombinant prenyltransferase CdpC3PT Organic and Biomolecular Chemistry 8 2010 2430 2438
29. X. Yu, and S.-M. Li Prenylation of flavonoids by using a dimethylallyltryptophan synthase 7-DMATS from Aspergillus fumigatus Chembiochem 12 2011 2280 2283
30. X. Yu, Y. Liu, X. Xie, X.-D. Zheng, and S.-M. Li Biochemical characterization of indole prenyltransferases: Filling the last gap of prenylation positions by a 5-dimethylallyl tryptophansynthase from Aspergillus clavatus The Journal of Biological Chemistry 287 2012 1371 1380
31. X. Yu, X. Xie, and S.-M. Li Substrate promiscuity of secondary metabolite enzymes: Prenylation of hydroxynaphthalenes by fungal indole prenyltransferases Applied Microbiology and Biotechnology 92 2011 737 748
32. H.-X. Zou, X.-L. Xie, U. Linne, X.-D. Zheng, and S.-M. Li Simultaneous C7- and N1-prenylation of cyclo-L-Trp-L-Trp catalyzed by a prenyltransferase from Aspergillus oryzae Organic and Biomolecular Chemistry 8 2010 3037 3044
33. H.-X. Zou, X. Xie, X.-D. Zheng, and S.-M. Li The tyrosine O-prenyltransferase SirD catalyzes O-, N-, and C-prenylations Applied Microbiology and Biotechnology 89 2011 1443 1451