Substrate promiscuity of secondary metabolite enzymes: Prenylation of hydroxynaphthalenes by fungal indole prenyltransferases

Applied Microbiology and Biotechnology

Volumn 92, Issue 4, 2011, Pages 737-748

  Yu, Xia ^a   Xie, Xiulan ^a   Li, Shu Ming ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

DMATS superfamily; Enzyme promiscuity; Fungal indole prenyltransferase; Prenylated hydroxynaphthalenes

Indexed keywords

CONVERSION RATES; CYCLIC DIPEPTIDE; DMATS SUPERFAMILY; ENZYME PRODUCTS; HYDROXYL GROUPS; INDOLE DERIVATIVES; PRENYLATED HYDROXYNAPHTHALENES; PRENYLATION; PRENYLTRANSFERASE; SECONDARY METABOLITES; STRUCTURE SIMILARITY; SYNTHASES; TURNOVER NUMBER;

AMINO ACIDS; ENZYME ACTIVITY; FUNGI; MASS SPECTROMETRY; METABOLITES; NAPHTHALENE; POLYPEPTIDES;

SUBSTRATES;

DIMETHYLALLYLTRANSFERASE; DIPEPTIDE; HYDROXYL GROUP; INDOLE; INDOLE DERIVATIVE; NAPHTHALENE DERIVATIVE;

CATALYSIS; ENZYME ACTIVITY; FUNGUS; HYDROXYL RADICAL; MASS SPECTROMETRY; METABOLITE; NAPHTHALENE; SUBSTRATE;

ARTICLE; ENZYME ACTIVITY; ENZYME METABOLISM; ENZYME SYNTHESIS; MASS SPECTROMETRY; METABOLITE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRENYLATION;

DIMETHYLALLYLTRANSTRANSFERASE; FUNGI; INDOLES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; NAPHTHOLS; PRENYLATION; SUBSTRATE SPECIFICITY;

EID: 82355183626     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-011-3351-y     Document Type: Article

References (36)

1. Berger S, Braun S (2004) 200 and more NMR experiments. A practical course. Weiley-VCH, Weinheim
2. Y Ding JR Wet J Cavalcoli S Li TJ Greshock KA Miller JM Finefield JD Sunderhaus TJ McAfoos S Tsukamoto RM Williams DH Sherman 2010 Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp J Am Chem Soc 132 12733 12740 10.1021/ja1049302 1:CAS:528:DC%2BC3cXhtVCnsL%2FP
3. A Grundmann S-M Li 2005 Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus Microbiology 151 2199 2207 10.1099/mic.0.27962-0 1:CAS:528:DC%2BD2MXmvV2muro%3D (Pubitemid 40984293)
4. Y Haagen I Unsöld L Westrich B Gust SB Richard JP Noel L Heide 2007 A soluble, magnesium-independent prenyltransferase catalyzes reverse and regular C-prenylations and O-prenylations of aromatic substrates FEBS Lett 581 2889 2893 10.1016/j.febslet.2007.05.031 1:CAS:528:DC%2BD2sXmsFyrtbo%3D (Pubitemid 46899029)
5. E Haug-Schifferdecker D Arican R Brueckner L Heide 2010 A new group of aromatic prenyltransferases in fungi, catalyzing a 2,7-dihydroxynaphthalene dimethylallyltransferase reaction J Biol Chem 285 16487 16494 10.1074/jbc.M110.113720 1:CAS:528:DC%2BC3cXmtlygs74%3D
6. L Heide 2009 Prenyl transfer to aromatic substrates: genetics and enzymology Curr Opin Chem Biol 13 171 179 10.1016/j.cbpa.2009.02.020 1:CAS:528:DC%2BD1MXlsVektrk%3D
7. M Jost G Zocher S Tarcz M Matuschek X Xie S-M Li T Stehle 2010 Structure-function analysis of an enzymatic prenyl transfer reaction identifies a reaction chamber with modifiable specificity J Am Chem Soc 132 17849 17858 10.1021/ja106817c 1:CAS:528:DC%2BC3cXhsVOgt7vL
8. A Kremer S-M Li 2008 Potential of a 7-dimethylallyltryptophan synthase as a tool for production of prenylated indole derivatives Appl Microbiol Biotechnol 79 951 961 10.1007/s00253-008-1505-3 1:CAS:528:DC%2BD1cXnslKgtLo%3D
9. A Kremer S-M Li 2010 A tyrosine O-prenyltransferase catalyses the first pathway-specific step in the biosynthesis of sirodesmin PL Microbiology 156 278 286 10.1099/mic.0.033886-0 1:CAS:528:DC%2BC3cXhvV2itrY%3D
10. A Kremer L Westrich S-M Li 2007 A 7-dimethylallyltryptophan synthase from Aspergillus fumigatus: overproduction, purification and biochemical characterization Microbiology 153 3409 3416 10.1099/mic.0.2007/009019-0 1:CAS:528:DC%2BD2sXht1SmurvL (Pubitemid 47629546)
11. T Kumano SB Richard JP Noel M Nishiyama T Kuzuyama 2008 Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities Bioorg Med Chem 16 8117 8126 10.1016/j.bmc.2008.07.052 1:CAS:528:DC%2BD1cXhtVyktbjO
12. T Kumano T Tomita M Nishiyama T Kuzuyama 2010 Functional characterization of the promiscuous prenyltransferase responsible for furaquinocin biosynthesis: identification of a physiological polyketide substrate and its prenylated reaction products J Biol Chem 285 39663 39671 10.1074/jbc.M110.153957 1:CAS:528:DC%2BC3cXhsFCht7bJ
13. T Kuzuyama JP Noel SB Richard 2005 Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products Nature 435 983 987 10.1038/nature03668 1:CAS:528:DC%2BD2MXltFeltbo%3D (Pubitemid 40896327)
14. S-M Li 2009 Applications of dimethylallyltryptophan synthases and other indole prenyltransferases for structural modification of natural products Appl Microbiol Biotechnol 84 631 639 10.1007/s00253-009-2128-z 1:CAS:528: DC%2BD1MXhtVygt7bK
15. S-M Li 2010 Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis Nat Prod Rep 27 57 78 10.1039/b909987p
16. PH Liang 2009 Reaction kinetics, catalytic mechanisms, conformational changes, and inhibitor design for prenyltransferases Biochemistry 48 6562 6570 10.1021/bi900371p 1:CAS:528:DC%2BD1MXnsFKnt7k%3D
17. A Macone E Lendaro A Comandini I Rovardi RM Matarese A Carraturo A Bonamore 2009 Chromane derivatives of small aromatic molecules: chemoenzymatic synthesis and growth inhibitory activity on human tumor cell line LoVo WT Bioorg Med Chem 17 6003 6007 10.1016/j.bmc.2009.06.061 1:CAS:528:DC%2BD1MXps1CrsLo%3D
18. U Metzger C Schall G Zocher I Unsöld E Stec S-M Li L Heide T Stehle 2009 The structure of dimethylallyl tryptophan synthase reveals a common architecture of aromatic prenyltransferases in fungi and bacteria Proc Natl Acad Sci USA 106 14309 14314 10.1073/pnas.0904897106 1:CAS:528:DC%2BD1MXhtFaiu7%2FE
19. U Metzger S Keller CE Stevenson L Heide DM Lawson 2010 Structure and mechanism of the magnesium-independent aromatic prenyltransferase CloQ from the clorobiocin biosynthetic pathway J Mol Biol 404 611 626 10.1016/j.jmb.2010.09. 067 1:CAS:528:DC%2BC3cXhsVGiu7fI
20. T Ozaki S Mishima M Nishiyama T Kuzuyama 2009 NovQ is a prenyltransferase capable of catalyzing the addition of a dimethylallyl group to both phenylpropanoids and flavonoids J Antibiot (Tokyo) 62 385 392 1:CAS:528:DC%2BD1MXptFCmsb0%3D
21. H-L Ruan W-B Yin J-Z Wu S-M Li 2008 Reinvestigation of a cyclic dipeptide N-prenyltransferase reveals rearrangement of N-1 prenylated indole derivatives Chembiochem 9 1044 1047 10.1002/cbic.200700723 1:CAS:528:DC%2BD1cXmtVWitb0%3D
22. H Sings S Singh 2003 Tremorgenic and nontremorgenic 2,3-fused indole diterpenoids Alkaloids Chem Biol 60 51 163 10.1016/S0099-9598(03)60002-7 1:CAS:528:DC%2BD3sXhtVWnsLrK (Pubitemid 137640335)
23. N Steffan S-M Li 2009 Increasing structure diversity of prenylated diketopiperazine derivatives by using a 4-dimethylallyltryptophan synthase Arch Microbiol 191 461 466 10.1007/s00203-009-0467-x 1:CAS:528:DC%2BD1MXkvFChsbg%3D
24. N Steffan IA Unsöld S-M Li 2007 Chemoenzymatic synthesis of prenylated indole derivatives by using a 4-dimethylallyltryptophan synthase from Aspergillus fumigatus Chembiochem 8 1298 1307 10.1002/cbic.200700107 1:CAS:528:DC%2BD2sXos12rsbc%3D (Pubitemid 47171997)
25. P Tudzynski K Holter T Correia C Arntz N Grammel U Keller 1999 Evidence for an ergot alkaloid gene cluster in Claviceps purpurea Mol Gen Genet 261 133 141 10.1007/s004380050950 1:CAS:528:DyaK1MXhsVylu7w%3D (Pubitemid 29137367)
26. IA Unsöld S-M Li 2005 Overproduction, purification and characterization of FgaPT2, a dimethylallyltryptophan synthase from Aspergillus fumigatus Microbiology 151 1499 1505 10.1099/mic.0.27759-0 (Pubitemid 40711797)
27. RM Williams EM Stocking JF Sanz-Cervera 2000 Biosynthesis of prenylated alkaloids derived from tryptophan Topics Curr Chem 209 97 173 10.1007/3-540-48146-X-3 1:CAS:528:DC%2BD3cXjs1Wltr4%3D
28. AB Woodside Z Huang CD Poulter 1988 Triammonium germanyl diphosphate Org Synth 66 211 215 1:CAS:528:DyaL1MXlslCns70%3D
29. K Yazaki K Sasaki Y Tsurumaru 2009 Prenylation of aromatic compounds, a key diversification of plant secondary metabolites Phytochemistry 70 1739 1745 10.1016/j.phytochem.2009.08.023 1:CAS:528:DC%2BD1MXhsVWls7fE
30. W-B Yin H-L Ruan L Westrich A Grundmann S-M Li 2007 CdpNPT, an N-prenyltransferase from Aspergillus fumigatus: overproduction, purification and biochemical characterisation Chembiochem 8 1154 1161 10.1002/cbic.200700079 1:CAS:528:DC%2BD2sXotlGhsbc%3D (Pubitemid 47194823)
31. W-B Yin A Grundmann J Cheng S-M Li 2009 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 284 100 109 10.1074/jbc.M807606200 1:CAS:528:DC%2BD1cXhsFCjtL7I
32. W-B Yin X-L Xie M Matuschek S-M Li 2010 Reconstruction of pyrrolo[2,3-b]indoles carrying an α-configured reverse C3-dimethylallyl moiety by using recombinant enzymes Org Biomol Chem 8 1133 1141 10.1039/b922440h 1:CAS:528:DC%2BC3cXitFGktrg%3D
33. W-B Yin X Yu X-L Xie S-M Li 2010 Preparation of pyrrolo[2,3-b]indoles carrying a ?-configured reverse C3-dimethylallyl moiety by using a recombinant prenyltransferase CdpC3PT Org Biomol Chem 8 2430 2438 10.1039/c000587h 1:CAS:528:DC%2BC3cXlslynsbk%3D
34. H Zou X Zheng S-M Li 2009 Substrate promiscuity of the cyclic dipeptide prenyltransferases from Aspergillus fumigatus J Nat Prod 72 44 52 10.1021/np800501m 1:CAS:528:DC%2BD1MXntlSg
35. H-X Zou X-L Xie U Linne X-D Zheng S-M Li 2010 Simultaneous C7- and N1-prenylation of cyclo-L-Trp-L-Trp catalyzed by a prenyltransferase from Aspergillus oryzae Org Biomol Chem 8 3037 3044 10.1039/c002850a 1:CAS:528:DC%2BC3cXnsFymtrc%3D
36. H-X Zou X Xie X-D Zheng S-M Li 2011 The tyrosine O-prenyltransferase SirD catalyzes O-, N-, and C-prenylations Appl Microbiol Biotechnol 89 1443 1451 10.1007/s00253-010-2956-x 1:CAS:528:DC%2BC3MXhslWltr0%3D