Catalytic mechanism of stereospecific formation of cis-configured prenylated pyrroloindoline diketopiperazines by indole prenyltransferases

Chemistry and Biology

Volumn 20, Issue 12, 2013, Pages 1492-1501

  Yu, Xia ^a   Zocher, Georg ^b   Xie, Xiulan ^a   Liebhold, Mike ^a   Schütz, Stefan ^b   Stehle, Thilo ^b   Li, Shu Ming ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYLALLYLTRANSFERASE; INDOLE DERIVATIVE; PIPERAZINEDIONE; PRENYLAMINE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; ENZYME ANALYSIS; ENZYME STRUCTURE; NONHUMAN; PRENYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM; STEREOSPECIFICITY;

ASPERGILLUS FUMIGATUS; BIOCATALYSIS; CRYSTALLOGRAPHY, X-RAY; DIKETOPIPERAZINES; DIMETHYLALLYLTRANSTRANSFERASE; DIPEPTIDES; INDOLES; MODELS, MOLECULAR; NEOSARTORYA; PEPTIDES, CYCLIC; PRENYLATION; PROLINE; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84890856196     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2013.10.007     Document Type: Article

References (37)

1. P.D. Adams, P.V. Afonine, G. Bunkóczi, V.B. Chen, I.W. Davis, N. Echols, J.J. Headd, L.W. Hung, G.J. Kapral, and R.W. Grosse-Kunstleve et al. PHENIX: a comprehensive Python-based system for macromolecular structure solution Acta Crystallogr. D Biol. Crystallogr. 66 2010 213 221
2. V.B. Chen, W.B. Arendall 3rd, J.J. Headd, D.A. Keedy, R.M. Immormino, G.J. Kapral, L.W. Murray, J.S. Richardson, and D.C. Richardson MolProbity: all-atom structure validation for macromolecular crystallography Acta Crystallogr. D Biol. Crystallogr. 66 2010 12 21
3. K.M. Depew, S.P. Marsden, D. Zatorska, A. Zatorski, W.G. Bornmann, and S.J. Danishefsky Total synthesis of 5-N-acetylardeemin and amauromine: Practical routes to potential MDR reversal agents J. Am. Chem. Soc. 121 1999 11953 11963
4. L. Du, X. Yang, T. Zhu, F. Wang, X. Xiao, H. Park, and Q. Gu Diketopiperazine alkaloids from a deep ocean sediment derived fungus Penicillium sp Chem. Pharm. Bull. (Tokyo) 57 2009 873 876
5. P. Emsley, B. Lohkamp, W.G. Scott, and K. Cowtan Features and development of Coot Acta Crystallogr. D Biol. Crystallogr. 66 2010 486 501
6. F. Gorrec The MORPHEUS protein crystallization screen J. Appl. Cryst. 42 2009 1035 1042
7. L. Holm, and P. Rosenström Dali server: conservation mapping in 3D Nucleic Acids Res. 38 Web Server issue 2010 W545 W549
8. M. Jost, G. Zocher, S. Tarcz, M. Matuschek, X. Xie, S.-M. Li, and T. Stehle Structure-function analysis of an enzymatic prenyl transfer reaction identifies a reaction chamber with modifiable specificity J. Am. Chem. Soc. 132 2010 17849 17858
9. W. Kabsch XDS Acta Crystallogr. D Biol. Crystallogr. 66 2010 125 132
10. S.-M. Li Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis Nat. Prod. Rep. 27 2010 57 78
11. T. Lindel, N. Marsch, and S.K. Adla Indole prenylation in alkaloid synthesis Top. Curr. Chem. 309 2012 67 129
12. H. Liu, and J.H. Naismith An efficient one-step site-directed deletion, insertion, single and multiple-site plasmid mutagenesis protocol BMC Biotechnol. 8 2008 91
13. A.J. McCoy, R.W. Grosse-Kunstleve, P.D. Adams, M.D. Winn, L.C. Storoni, and R.J. Read Phaser crystallographic software J. Appl. Cryst. 40 2007 658 674
14. U. Metzger, C. Schall, G. Zocher, I. Unsöld, E. Stec, S.-M. Li, L. Heide, and T. Stehle The structure of dimethylallyl tryptophan synthase reveals a common architecture of aromatic prenyltransferases in fungi and bacteria Proc. Natl. Acad. Sci. USA 106 2009 14309 14314
15. G.N. Murshudov, A.A. Vagin, and E.J. Dodson Refinement of macromolecular structures by the maximum-likelihood method Acta Crystallogr. D Biol. Crystallogr. 53 1997 240 255
16. M. O'Brien, K.F. Nielsen, P. O'Kiely, P.D. Forristal, H.T. Fuller, and J.C. Frisvad Mycotoxins and other secondary metabolites produced in vitro by Penicillium paneum Frisvad and Penicillium roqueforti Thom isolated from baled grass silage in Ireland J. Agric. Food Chem. 54 2006 9268 9276
17. T.A. Reshetilova, N.G. Vinokurova, V.N. Khmelenina, and A.G. Kozlovskii The role of roquefortine in the synthesis of alkaloids, meleagrine, glandicolines A and B, and oxaline in Penicillum glandicola and P. atramentosum Microbiology (Moscow) 64 1995 27 29
18. P. Ruiz-Sanchis, S.A. Savina, F. Albericio, and M. Álvarez Structure, bioactivity and synthesis of natural products with hexahydropyrrolo[2,3-b]indole Chemistry 17 2011 1388 1408
19. C.L. Schardl, D.G. Panaccione, and P. Tudzynski Ergot alkaloids - biology and molecular biology Alkaloids Chem. Biol. 63 2006 45 86
20. J.M. Schuller, G. Zocher, M. Liebhold, X. Xie, M. Stahl, S.-M. Li, and T. Stehle Structure and catalytic mechanism of a cyclic dipeptide prenyltransferase with broad substrate promiscuity J. Mol. Biol. 422 2012 87 99
21. A.W. Schüttelkopf, and D.M. van Aalten PRODRG: a tool for high-throughput crystallography of protein-ligand complexes Acta Crystallogr. D Biol. Crystallogr. 60 2004 1355 1363
22. P.M. Scott, and P.C. Kennedy Analysis of blue cheese for roquefortine and other alkaloids from Penicillium roqueforti J. Agric. Food Chem. 24 1976 865 868
23. S. Takase, Y. Kawai, I. Uchida, H. Tanaka, and H. Aoki Structure of amauromine, a new hypotensive vasodilator produced by Amauroascus sp Tetrahedron 41 1985 3037 3048
24. S. Uhlig, C.J. Botha, T. Vrålstad, E. Rolén, and C.O. Miles Indole-diterpenes and ergot alkaloids in Cynodon dactylon (Bermuda grass) infected with Claviceps cynodontis from an outbreak of tremors in cattle J. Agric. Food Chem. 57 2009 11112 11119
25. D. Wakana, T. Hosoe, T. Itabashi, K. Nozawa, K. Okada, G.M.C. Takaki, T. Yaguchi, K. Fukushima, and K.I. Kawai Isolation of isoterrein from Neosartorya fischeri Mycotoxins 56 2006 3 6
26. C. Wallwey, and S.-M. Li Ergot alkaloids: structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes Nat. Prod. Rep. 28 2011 496 510
27. R.M. Williams, E.M. Stocking, and J.F. Sanz-Cervera Biosynthesis of prenylated alkaloids derived from tryptophan Top. Curr. Chem. 209 2000 97 173
28. M.D. Winn, C.C. Ballard, K.D. Cowtan, E.J. Dodson, P. Emsley, P.R. Evans, R.M. Keegan, E.B. Krissinel, A.G. Leslie, and A. McCoy et al. Overview of the CCP4 suite and current developments Acta Crystallogr. D Biol. Crystallogr. 67 2011 235 242
29. B. Wollinsky, L. Ludwig, A. Hamacher, X. Yu, M.U. Kassack, and S.-M. Li Prenylation at the indole ring leads to a significant increase of cytotoxicity of tryptophan-containing cyclic dipeptides Bioorg. Med. Chem. Lett. 22 2012 3866 3869
30. B. Wollinsky, L. Ludwig, X. Xie, and S.-M. Li 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
31. A.B. Woodside, Z. Huang, and C.D. Poulter Trisammonium geranyl diphosphate Org. Synth. 66 1988 211 215
32. 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
33. W.-B. Yin, J. Cheng, and S.-M. Li Stereospecific synthesis of aszonalenins by using two recombinant prenyltransferases Org. Biomol. Chem. 7 2009 2202 2207
34. 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 J. Biol. Chem. 284 2009 100 109
35. W.-B. Yin, X.-L. Xie, M. Matuschek, and S.-M. Li Reconstruction of pyrrolo[2,3-b]indoles carrying an α-configured reverse C3-dimethylallyl moiety by using recombinant enzymes Org. Biomol. Chem. 8 2010 1133 1141
36. W.-B. Yin, X. Yu, X.-L. Xie, and S.-M. Li Preparation of pyrrolo[2,3-b]indoles carrying a β-configured reverse C3-dimethylallyl moiety by using a recombinant prenyltransferase CdpC3PT Org. Biomol. Chem. 8 2010 2430 2438
37. S. Yin, X. Yu, Q. Wang, X.Q. Liu, and S.-M. Li Identification of a brevianamide F reverse prenyltransferase BrePT from Aspergillus versicolor with a broad substrate specificity towards tryptophan-containing cyclic dipeptides Appl. Microbiol. Biotechnol. 97 2013 1649 1660