A promiscuous prenyltransferase from Aspergillus oryzae catalyses C-prenylations of hydroxynaphthalenes in the presence of different prenyl donors

Applied Microbiology and Biotechnology

Volumn 98, Issue 11, 2014, Pages 4987-4994

  Pockrandt, Daniel ^a   Sack, Christopher ^a   Kosiol, Tatjana ^a   Li, Shu Ming ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

DMATS superfamily; Enzyme catalysis; Hydroxynaphthalene; Prenyl donor

Indexed keywords

ASPERGILLUS; BIOCHEMISTRY; ENZYMES; SUBSTRATES;

DMATS SUPERFAMILY; ENZYME CATALYSIS; FARNESYL DIPHOSPHATE; HYDROXYNAPHTHALENE; PRENYL DONOR; PRENYLATION REACTIONS; SECONDARY METABOLITES; SUBSTRATE SPECIFICITY;

CATALYSIS;

DIMETHYLALLYL DIPHOSPHATE; DIMETHYLALLYLTRANSFERASE; FARNESYL DIPHOSPHATE; FUNGAL ENZYME; GERANYL DIPHOSPHATE; HYDROXYNAPHTHALENE DERIVATIVE; NAPHTHALENE DERIVATIVE; PRENYLAMINE; PYROPHOSPHORIC ACID DERIVATIVE; UNCLASSIFIED DRUG; 3,3-DIMETHYLALLYL PYROPHOSPHATE; DITERPENE; HEMITERPENE; ISOPRENOID PHOSPHATE; NAPHTHOL DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; SESQUITERPENE;

CATALYSIS; ENZYME ACTIVITY; FUNGUS; SECONDARY METABOLITE; SUBSTRATE;

ARTICLE; ASPERGILLUS ORYZAE; CATALYSIS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME SPECIFICITY; NONHUMAN; PRENYLATION; PROTEIN FUNCTION; ENZYMOLOGY; METABOLISM;

ASPERGILLUS ORYZAE; NEOSARTORYA FISCHERI;

ASPERGILLUS ORYZAE; DIMETHYLALLYLTRANSTRANSFERASE; DIPHOSPHATES; DITERPENES; HEMITERPENES; NAPHTHOLS; ORGANOPHOSPHORUS COMPOUNDS; POLYISOPRENYL PHOSPHATES; PRENYLATION; SESQUITERPENES;

EID: 84901659071     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-014-5509-x     Document Type: Article

References (34)

1. Botta B, Vitali A, Menendez P, Misiti D, Delle MG (2005) Prenylated flavonoids: pharmacology and biotechnology. Curr Med Chem 12: 717-739
2. Chooi YH, Tang Y (2012) Navigating the fungal polyketide chemical space: from genes to molecules. J Org Chem 77:9933-9953
3. Chooi YH, Cacho R, TangY (2010) Identification of the viridicatumtoxin and griseofulvin gene clusters from Penicillium aethiopicum. Chem Biol 17:483-494
4. Chooi YH, Wang P, Fang J, Li Y, Wu K, Wang P, Tang Y (2012) Discovery and characterization of a group of fungal polycyclic polyketide prenyltransferases. J Am Chem Soc 134:9428-9437
5. Chooi YH, Fang J, Liu H, Filler SG, Wang P, Tang Y (2013) Genome mining of a prenylated and immunosuppressive polyketide from pathogenic fungi. Org Lett 15:780-783
6. Condurso HL, Bruner SD (2012) Structure and noncanonical chemistry of nonribosomal peptide biosynthetic machinery. Nat Prod Rep 29: 1099-1110
7. Fujii I, Mori Y, Watanabe A, Kubo Y, Tsuji G, Ebizuka Y (2000) Enzymatic synthesis of 1,3,6,8-tetrahydroxynaphthalene solely from malonyl coenzyme A by a fungal iterative type I polyketide synthase PKS1. Biochemistry 39:8853-8858 (Pubitemid 30602795)
8. Galagan JE, Calvo SE, Cuomo C, Ma LJ, Wortman JR, Batzoglou S, Lee SI, Basturkmen M, Spevak CC, Clutterbuck J, Kapitonov V, Jurka J, Scazzocchio C, Farman M, Butler J, Purcell S, Harris S, Braus GH, Draht O, Busch S, d'Enfert C, Bouchier C, Goldman GH, Bell-Pedersen D, Griffiths-Jones S, Doonan JH, Yu J, Vienken K, Pain A, Freitag M, Selker EU, Archer DB, Penalva MA, Oakley BR, Momany M, Tanaka T, Kumagai T, Asai K, Machida M, Nierman WC, Denning DW, Caddick M, Hynes M, Paoletti M, Fischer R, Miller B, Dyer P, Sachs MS, Osmani SA, Birren BW (2005) Sequencing of Aspergillus nidulans and comparative analysis with A. fumigatus and A. oryzae. Nature 438: 1105-1115 (Pubitemid 41831674)
9. Haagen Y, Unsöld I, Westrich L, Gust B, Richard SB, Noel JP, Heide L (2007) A soluble, magnesium-independent prenyltransferase catalyzes reverse and regular C-prenylations and O-prenylations of aromatic substrates. FEBS Lett 581:2889-2893 (Pubitemid 46899029)
10. Haug-Schifferdecker E, Arican D, Brueckner R, Heide L (2010) A new group of aromatic prenyltransferases in fungi, catalyzing a 2,7-dihydroxynaphthalene dimethylallyltransferase reaction. J Biol Chem 285:16487-16494
11. Hussein AA, Bozzi B, Correa M, Capson TL, Kursar TA, Coley PD, Solis PN, Gupta MP (2003) Bioactive constituents from three Vismia species. J Nat Prod 66:858-860 (Pubitemid 36782098)
12. Hussein AA, Barberena I, Capson TL, Kursar TA, Coley PD, Solis PN, Gupta MP (2004) New cytotoxic naphthopyrane derivatives from Adenaria floribunda. J Nat Prod 67:451-453 (Pubitemid 38405713)
13. Kremer A, Li S-M (2010) A tyrosine O-prenyltransferase catalyses the first pathway-specific step in the biosynthesis of sirodesmin PL. Microbiology 156:278-286
14. Kumano T, Richard SB, Noel JP, Nishiyama M, Kuzuyama T (2008) Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities. Bioorg Med Chem 16:8117-8126
15. Kumano T, Tomita T, Nishiyama M, Kuzuyama T (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
16. Kuzuyama T, Noel JP, Richard SB (2005) Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products. Nature 435:983-987 (Pubitemid 40896327)
17. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680-685
18. Li S-M (2009) Applications of dimethylallyltryptophan synthases and other indole prenyltransferases for structural modification of natural products. Appl Microbiol Biotechnol 84:631-639
19. Liebhold M, Li S-M (2013) Regiospecific benzylation of tryptophan and derivatives catalyzed by a fungal dimethylallyl transferase. Org Lett 15:5834-5837
20. Liebhold M, Xie X, Li S-M (2012) Expansion of enzymatic Friedel-Crafts alkylation on indoles: acceptance of unnatural beta-unsaturated allyl diphospates by dimethylallyl-tryptophan synthases. Org Lett 14:4884-4885
21. Liebhold M, Xie X, Li S-M (2013) Breaking cyclic dipeptide prenyltransferase regioselectivity by unnatural alkyl donors. Org. Lett. 15. DOI:10.1021/ol401247s
22. Machida M, Asai K, Sano M, Tanaka T, Kumagai T, Terai G, Kusumoto K, Arima T, Akita O, Kashiwagi Y, Abe K, Gomi K, Horiuchi H, Kitamoto K, Kobayashi T, Takeuchi M, Denning DW, Galagan JE, Nierman WC, Yu J, Archer DB, Bennett JW, Bhatnagar D, Cleveland TE, Fedorova ND, Gotoh O, Horikawa H, Hosoyama A, Ichinomiya M, Igarashi R, Iwashita K, Juvvadi PR, KatoM, Kato Y, Kin T, Kokubun A, Maeda H, Maeyama N, Maruyama J, Nagasaki H, Nakajima T, Oda K, Okada K, Paulsen I, Sakamoto K, Sawano T, Takahashi M, Takase K, Terabayashi Y, Wortman JR, Yamada O, Yamagata Y, Anazawa H, Hata Y, Koide Y, Komori T, Koyama Y, Minetoki T, Suharnan S, Tanaka A, Isono K, Kuhara S, Ogasawara N, Kikuchi H (2005) Genome sequencing and analysis of Aspergillus oryzae. Nature 438:1157-1161 (Pubitemid 41831685)
23. Pockrandt D, Li S-M (2013) Geranylation of cyclic dipeptides by the dimethylallyl transferase AnaPT resulting in a shift of prenylation position on the indole ring. Chembiochem 14:2023-2028
24. Pockrandt D, Ludwig L, Fan A, Konig GM, Li S-M(2012) New insights into the biosynthesis of prenylated xanthones: XptB from Aspergillus nidulans catalyses an O-prenylation of xanthones. Chembiochem 13:2764-2771
25. Sambrook J, Russell DW (2001) Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory Press, New York
26. Sanchez JF, Entwistle R, Hung JH, Yaegashi J, Jain S, Chiang YM, Wang CC, Oakley BR (2011) Genome-based deletion analysis reveals the prenyl xanthone biosynthesis pathway in Aspergillus nidulans. JAm Chem Soc 133:4010-4017
27. Shin-Ya K, Imai S, Furihata K, Hayakawa Y, Kato Y, Vanduyne GD, Clardy J, Seto H (1990) Isolation and structural elucidation of an antioxidative agent, naphterpin. J Antibiot 43:444-447 (Pubitemid 20182406)
28. Steffan N, Grundmann A, Yin W-B, Kremer A, Li S-M (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
29. Woodside AB, Huang Z, Poulter CD (1988) Trisammonium geranyl diphosphate. Org Synth 66:211-215
30. Yu X, Li S-M (2011) Prenylation of flavonoids by using a dimethylallyltryptophan synthase 7-DMATS from Aspergillus fumigatus. Chembiochem 12:2280-2283
31. Yu X, Li S-M (2012) Prenyltransferases of the dimethylallyltryptophan synthase superfamily. Methods Enzymol 516:259-278
32. Yu X, Xie X, Li S-M (2011) Substrate promiscuity of secondary metabolite enzymes: prenylation of hydroxynaphthalenes by fungal indole prenyltransferases. Appl Microbiol Biotechnol 92:737-748
33. Yu X, Liu Y, Xie X, Zheng X-D, Li S-M (2012) Biochemical characterization of indole prenyltransferases: filling the last gap of prenylation positions by a 5-dimethylallyltryptophan synthase from Aspergillus clavatus. J Biol Chem 287:1371-1380
34. Zou H-X, Xie X, Zheng X-D, Li S-M (2011) The tyrosine O-prenyltransferase SirD catalyzes O-, N-, and C-prenylations. Appl Microbiol Biotechnol 89:1443-1451