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Volumn 84, Issue 4, 2009, Pages 631-639

Applications of dimethylallyltryptophan synthases and other indole prenyltransferases for structural modification of natural products

Author keywords

Aspergillus; Chemoenzymatic synthesis; Cyclic dipeptide; Diketopiperazine; Dimethylallyltryptophan synthase; Indole alkaloid; Indole derivatives; Neosartorya; Prenyltransferase

Indexed keywords

ASPERGILLUS; CHEMOENZYMATIC SYNTHESIS; CYCLIC DIPEPTIDE; DIKETOPIPERAZINE; DIMETHYLALLYLTRYPTOPHAN SYNTHASE; INDOLE ALKALOID; INDOLE DERIVATIVES; NEOSARTORYA; PRENYLTRANSFERASE;

EID: 69949164572     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-009-2128-z     Document Type: Short Survey
Times cited : (55)

References (53)
  • 1
    • 33748286847 scopus 로고    scopus 로고
    • Impact of Aspergillus oryza genomics on industrial production of metabolites
    • K Abe K Gomi F Hasegawa M Machida 2006 Impact of Aspergillus oryza genomics on industrial production of metabolites Mycopathologia 162 143 153
    • (2006) Mycopathologia , vol.162 , pp. 143-153
    • Abe, K.1    Gomi, K.2    Hasegawa, F.3    MacHida, M.4
  • 3
    • 27744589213 scopus 로고    scopus 로고
    • Novel prenyltransferase enzymes as a tool for flavonoid prenylation
    • B Botta GD Monache P Menendez A Boffi 2005 Novel prenyltransferase enzymes as a tool for flavonoid prenylation Trends Pharmacol Sci 26 606 608
    • (2005) Trends Pharmacol Sci , vol.26 , pp. 606-608
    • Botta, B.1    Monache, G.D.2    Menendez, P.3    Boffi, A.4
  • 4
    • 1942454465 scopus 로고    scopus 로고
    • Current strategies for the prevention of postpartum haemorrhage in the third stage of labour
    • YS Chong LL Su S Arulkumaran 2004 Current strategies for the prevention of postpartum haemorrhage in the third stage of labour Curr Opin Obstet Gynecol 16 143 150
    • (2004) Curr Opin Obstet Gynecol , vol.16 , pp. 143-150
    • Chong, Y.S.1    Su, L.L.2    Arulkumaran, S.3
  • 7
    • 0030036459 scopus 로고    scopus 로고
    • Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus: II. physico-chemical properties and structures
    • CB Cui H Kakeya H Osada 1996 Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures J Antibiot 49 534 540 (Pubitemid 26235661)
    • (1996) Journal of Antibiotics , vol.49 , Issue.6 , pp. 534-540
    • Cui, C.-B.1    Kakeya, H.2    Osada, H.3
  • 8
    • 47049111183 scopus 로고    scopus 로고
    • Molecular analysis of a 4-dimethylallyltryptophan synthase from Malbranchea aurantiaca
    • Y Ding RM Williams DH Sherman 2008 Molecular analysis of a 4-dimethylallyltryptophan synthase from Malbranchea aurantiaca J Biol Chem 283 16068 16076
    • (2008) J Biol Chem , vol.283 , pp. 16068-16076
    • Ding, Y.1    Williams, R.M.2    Sherman, D.H.3
  • 9
    • 0026751389 scopus 로고
    • Purification and characterization of dimethylallyl tryptophan synthase from Claviceps purpurea
    • JC Gebler CD Poulter 1992 Purification and characterization of dimethylallyl tryptophan synthase from Claviceps purpurea Arch Biochem Biophys 296 308 313
    • (1992) Arch Biochem Biophys , vol.296 , pp. 308-313
    • Gebler, J.C.1    Poulter, C.D.2
  • 10
    • 0142106002 scopus 로고    scopus 로고
    • Migraine: Diagnosis and management
    • PJ Goadsby 2003 Migraine: diagnosis and management Intern Med J 33 436 442
    • (2003) Intern Med J , vol.33 , pp. 436-442
    • Goadsby, P.J.1
  • 11
    • 22144479730 scopus 로고    scopus 로고
    • Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus
    • A Grundmann S-M Li 2005 Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus Microbiology 151 2199 2207
    • (2005) Microbiology , vol.151 , pp. 2199-2207
    • Grundmann, A.1    Li, S.-M.2
  • 12
    • 54349101019 scopus 로고    scopus 로고
    • FtmPT2, an N-prenyltransferase from Aspergillus fumigatus, catalyses the last step in the biosynthesis of fumitremorgin B
    • A Grundmann T Kuznetsova SS Afiyatullov S-M Li 2008 FtmPT2, an N-prenyltransferase from Aspergillus fumigatus, catalyses the last step in the biosynthesis of fumitremorgin B Chembiochem 9 2059 2063
    • (2008) Chembiochem , vol.9 , pp. 2059-2063
    • Grundmann, A.1    Kuznetsova, T.2    Afiyatullov, S.S.3    Li, S.-M.4
  • 13
    • 65349101892 scopus 로고    scopus 로고
    • Prenyl transfer to aromatic substrates: Genetics and enzymology
    • L Heide 2009 Prenyl transfer to aromatic substrates: genetics and enzymology Curr Opin Chem Biol 13 171 179
    • (2009) Curr Opin Chem Biol , vol.13 , pp. 171-179
    • Heide, L.1
  • 14
    • 0015116740 scopus 로고
    • Isolation of dimethylallylpyrophosphate: Tryptophan dimethylallyl transferase from the ergot fungus (Claviceps spec.)
    • PF Heinstein SI Lee HG Floss 1971 Isolation of dimethylallylpyrophosphate: tryptophan dimethylallyl transferase from the ergot fungus (Claviceps spec.) Biochem Biophys Res Commun 44 1244 1251
    • (1971) Biochem Biophys Res Commun , vol.44 , pp. 1244-1251
    • Heinstein, P.F.1    Lee, S.I.2    Floss, H.G.3
  • 15
    • 0021360027 scopus 로고
    • Production of fumigaclavine A by Aspergillus tamarii Kita
    • KK Janardhanan A Sattar A Husain 1984 Production of fumigaclavine A by Aspergillus tamarii Kita Can J Microbiol 30 247 250
    • (1984) Can J Microbiol , vol.30 , pp. 247-250
    • Janardhanan, K.K.1    Sattar, A.2    Husain, A.3
  • 16
    • 33846282735 scopus 로고    scopus 로고
    • The first filamentous fungal genome sequences: Aspergillus leads the way for essential everyday resources or dusty museum specimens?
    • MG Jones 2007 The first filamentous fungal genome sequences: Aspergillus leads the way for essential everyday resources or dusty museum specimens? Microbiology 153 1 6
    • (2007) Microbiology , vol.153 , pp. 1-6
    • Jones, M.G.1
  • 17
    • 30544434099 scopus 로고    scopus 로고
    • Fungal secondary metabolism-from biochemistry to genomics
    • NP Keller G Turner JW Bennett 2005 Fungal secondary metabolism-from biochemistry to genomics Nat Rev Microbiol 3 937 947
    • (2005) Nat Rev Microbiol , vol.3 , pp. 937-947
    • Keller, N.P.1    Turner, G.2    Bennett, J.W.3
  • 18
    • 33644934032 scopus 로고    scopus 로고
    • Manipulation of prenyl chain length determination mechanism of cis-prenyltransferases
    • Y Kharel S Takahashi S Yamashita T Koyama 2006 Manipulation of prenyl chain length determination mechanism of cis-prenyltransferases FEBS J 273 647 657
    • (2006) FEBS J , vol.273 , pp. 647-657
    • Kharel, Y.1    Takahashi, S.2    Yamashita, S.3    Koyama, T.4
  • 19
    • 0031687689 scopus 로고    scopus 로고
    • Effects of tryprostatin derivatives on microtubule assembly in vitro and in situ
    • M Kondoh T Usui T Mayumi H Osada 1998 Effects of tryprostatin derivatives on microtubule assembly in vitro and in situ J Antibiot 51 801 804
    • (1998) J Antibiot , vol.51 , pp. 801-804
    • Kondoh, M.1    Usui, T.2    Mayumi, T.3    Osada, H.4
  • 20
    • 46149117250 scopus 로고    scopus 로고
    • Potential of a 7-dimethylallyltryptophan synthase as a tool for production of prenylated indole derivatives
    • 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
    • (2008) Appl Microbiol Biotechnol , vol.79 , pp. 951-961
    • Kremer, A.1    Li, S.-M.2
  • 21
    • 35448932356 scopus 로고    scopus 로고
    • A 7-dimethylallyltryptophan synthase from Aspergillus fumigatus: Overproduction, purification and biochemical characterization
    • DOI 10.1099/mic.0.2007/009019-0
    • A Kremer L Westrich S-M Li 2007 A 7-dimethylallyltryptophan synthase from Aspergillus fumigatus: overproduction, purification and biochemical characterization Microbiology 153 3409 3416 (Pubitemid 47629546)
    • (2007) Microbiology , vol.153 , Issue.10 , pp. 3409-3416
    • Kremer, A.1    Westrich, L.2    Li, S.-M.3
  • 22
    • 0017176386 scopus 로고
    • Purification and properties of dimethylallylpyrophosphate: Tryptophan dimethylallyl transferase, the first enzyme of ergot alkaloid biosynthesis in Claviceps sp. SD 58
    • SL Lee HG Floss P Heinstein 1976 Purification and properties of dimethylallylpyrophosphate: tryptophan dimethylallyl transferase, the first enzyme of ergot alkaloid biosynthesis in Claviceps sp. SD 58 Arch Biochem Biophys 177 84 94
    • (1976) Arch Biochem Biophys , vol.177 , pp. 84-94
    • Lee, S.L.1    Floss, H.G.2    Heinstein, P.3
  • 23
    • 67650410702 scopus 로고    scopus 로고
    • Evolution of aromatic prenyltransferases in the biosynthesis of indole derivatives
    • in press
    • Li S-M (2009) Evolution of aromatic prenyltransferases in the biosynthesis of indole derivatives. Phytochemistry (in press)
    • (2009) Phytochemistry
    • Li, S.-M.1
  • 24
    • 0036375597 scopus 로고    scopus 로고
    • Structure, mechanism and function of prenyltransferases
    • PH Liang TP Ko AH Wang 2002 Structure, mechanism and function of prenyltransferases Eur J Biochem 269 3339 3354
    • (2002) Eur J Biochem , vol.269 , pp. 3339-3354
    • Liang, P.H.1    Ko, T.P.2    Wang, A.H.3
  • 25
    • 58149492519 scopus 로고    scopus 로고
    • Different reaction mechanisms for cis- and trans-prenyltransferases
    • YP Lu HG Liu PH Liang 2009 Different reaction mechanisms for cis- and trans-prenyltransferases Biochem Biophys Res Commun 379 351 355
    • (2009) Biochem Biophys Res Commun , vol.379 , pp. 351-355
    • Lu, Y.P.1    Liu, H.G.2    Liang, P.H.3
  • 26
    • 33645974330 scopus 로고    scopus 로고
    • Endophytic fungal metabolite fumigaclavine C causes relaxation of isolated rat aortic rings
    • HY Ma YC Song YY Mao JH Jiang RX Tan L Luo 2006 Endophytic fungal metabolite fumigaclavine C causes relaxation of isolated rat aortic rings Planta Med 72 387 392
    • (2006) Planta Med , vol.72 , pp. 387-392
    • Ma, H.Y.1    Song, Y.C.2    Mao, Y.Y.3    Jiang, J.H.4    Tan, R.X.5    Luo, L.6
  • 27
    • 34347218222 scopus 로고    scopus 로고
    • Protein isoprenylation in biology and disease: General overview and perspectives from studies with genetically engineered animals
    • D Perez-Sala 2007 Protein isoprenylation in biology and disease: general overview and perspectives from studies with genetically engineered animals Front Biosci 12 4456 4472
    • (2007) Front Biosci , vol.12 , pp. 4456-4472
    • Perez-Sala, D.1
  • 30
    • 46149105053 scopus 로고    scopus 로고
    • Reinvestigation of a cyclic dipeptide N-prenyltransferase reveals rearrangement of N-1 prenylated indole derivatives
    • 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
    • (2008) Chembiochem , vol.9 , pp. 1044-1047
    • Ruan, H.-L.1    Yin, W.-B.2    Wu, J.-Z.3    Li, S.-M.4
  • 31
    • 48949120151 scopus 로고    scopus 로고
    • Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens
    • K Sasaki K Mito K Ohara H Yamamoto K Yazaki 2008 Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens Plant Physiol 146 1075 1084
    • (2008) Plant Physiol , vol.146 , pp. 1075-1084
    • Sasaki, K.1    Mito, K.2    Ohara, K.3    Yamamoto, H.4    Yazaki, K.5
  • 33
    • 38849108030 scopus 로고    scopus 로고
    • The Aspergillus nidulans enzyme TdiB catalyzes prenyltransfer to the precursor of bioactive asterriquinones
    • P Schneider M Weber D Hoffmeister 2008 The Aspergillus nidulans enzyme TdiB catalyzes prenyltransfer to the precursor of bioactive asterriquinones Fungal Genet Biol 45 302 309
    • (2008) Fungal Genet Biol , vol.45 , pp. 302-309
    • Schneider, P.1    Weber, M.2    Hoffmeister, D.3
  • 34
    • 67349244074 scopus 로고    scopus 로고
    • Increasing structure diversity of prenylated diketopiperazine derivatives by using a 4-dimethylallyltryptophan synthase
    • N Steffan S-M Li 2009 Increasing structure diversity of prenylated diketopiperazine derivatives by using a 4-dimethylallyltryptophan synthase Arch Microbiol 191 461 466
    • (2009) Arch Microbiol , vol.191 , pp. 461-466
    • Steffan, N.1    Li, S.-M.2
  • 35
    • 34547450158 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of prenylated indole derivatives by using a 4-dimethylallyltryptophan synthase from Aspergillus fumigatus
    • 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
    • (2007) Chembiochem , vol.8 , pp. 1298-1307
    • Steffan, N.1    Unsöld, I.A.2    Li, S.-M.3
  • 36
    • 62349088498 scopus 로고    scopus 로고
    • Indole prenyltransferases from fungi: A new enzyme group with high potential for the production of prenylated indole derivatives
    • N Steffan A Grundmann W-B Yin A Kremer S-M Li 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
    • (2009) Curr Med Chem , vol.16 , pp. 218-231
    • Steffan, N.1    Grundmann, A.2    Yin, W.-B.3    Kremer, A.4    Li, S.-M.5
  • 37
    • 33748564953 scopus 로고    scopus 로고
    • Structure and function of cis-prenyl chain elongating enzymes
    • S Takahashi T Koyama 2006 Structure and function of cis-prenyl chain elongating enzymes Chem Rec 6 194 205
    • (2006) Chem Rec , vol.6 , pp. 194-205
    • Takahashi, S.1    Koyama, T.2
  • 38
    • 0028858379 scopus 로고
    • The Claviceps purpurea gene encoding dimethylallyltryptophan synthase, the committed step for ergot alkaloid biosynthesis
    • HF Tsai H Wang JC Gebler CD Poulter CL Schardl 1995 The Claviceps purpurea gene encoding dimethylallyltryptophan synthase, the committed step for ergot alkaloid biosynthesis Biochem Biophys Res Commun 216 119 125
    • (1995) Biochem Biophys Res Commun , vol.216 , pp. 119-125
    • Tsai, H.F.1    Wang, H.2    Gebler, J.C.3    Poulter, C.D.4    Schardl, C.L.5
  • 41
    • 19044365898 scopus 로고    scopus 로고
    • Overproduction, purification and characterization of FgaPT2, a dimethylallyltryptophan synthase from Aspergillus fumigatus
    • IA Unsöld S-M Li 2005 Overproduction, purification and characterization of FgaPT2, a dimethylallyltryptophan synthase from Aspergillus fumigatus Microbiology 151 1499 1505
    • (2005) Microbiology , vol.151 , pp. 1499-1505
    • Unsöld, I.A.1    Li, S.-M.2
  • 42
    • 30444438065 scopus 로고    scopus 로고
    • Reverse prenyltransferase in the biosynthesis of fumigaclavine C in Aspergillus fumigatus: Gene expression, purification and characterization of fumigaclavine C synthase FgaPT1
    • IA Unsöld S-M Li 2006 Reverse prenyltransferase in the biosynthesis of fumigaclavine C in Aspergillus fumigatus: gene expression, purification and characterization of fumigaclavine C synthase FgaPT1 Chembiochem 7 158 164
    • (2006) Chembiochem , vol.7 , pp. 158-164
    • Unsöld, I.A.1    Li, S.-M.2
  • 43
    • 0032143275 scopus 로고    scopus 로고
    • Tryprostatin A, a specific and novel inhibitor of microtubule assembly
    • T Usui M Kondoh CB Cui T Mayumi H Osada 1998 Tryprostatin A, a specific and novel inhibitor of microtubule assembly Biochem J 333 543 548 (Pubitemid 28398519)
    • (1998) Biochemical Journal , vol.333 , Issue.3 , pp. 543-548
    • Usui, T.1    Kondoh, M.2    Cui, C.-B.3    Mayumi, T.4    Osada, H.5
  • 44
    • 3543013226 scopus 로고    scopus 로고
    • The Penicillium commune Thom and Penicillium clavigerum demelius fungi producing fumigaclavines A and B
    • NG Vinokurova SM Ozerskaya BP Baskunov MU Arinbasarov 2003 The Penicillium commune Thom and Penicillium clavigerum demelius fungi producing fumigaclavines A and B Microbiology (Moscow) 72 149 151
    • (2003) Microbiology (Moscow) , vol.72 , pp. 149-151
    • Vinokurova, N.G.1    Ozerskaya, S.M.2    Baskunov, B.P.3    Arinbasarov, M.U.4
  • 45
    • 0346725108 scopus 로고    scopus 로고
    • The determinant step in ergot alkaloid biosynthesis by an endophyte of perennial ryegrass
    • J Wang C Machado DG Panaccione HF Tsai CL Schardl 2004 The determinant step in ergot alkaloid biosynthesis by an endophyte of perennial ryegrass Fungal Genet Biol 41 189 198
    • (2004) Fungal Genet Biol , vol.41 , pp. 189-198
    • Wang, J.1    MacHado, C.2    Panaccione, D.G.3    Tsai, H.F.4    Schardl, C.L.5
  • 47
    • 22044435268 scopus 로고    scopus 로고
    • Fumigaclavine C, an fungal metabolite, improves experimental colitis in mice via downregulating Th1 cytokine production and matrix metalloproteinase activity
    • X-F Wu M-J Fei R-G Shu R-X Tan Q Xu 2005 Fumigaclavine C, an fungal metabolite, improves experimental colitis in mice via downregulating Th1 cytokine production and matrix metalloproteinase activity Int Immunopharmacol 5 1543 1553
    • (2005) Int Immunopharmacol , vol.5 , pp. 1543-1553
    • Wu, X.-F.1    Fei, M.-J.2    Shu, R.-G.3    Tan, R.-X.4    Xu, Q.5
  • 48
    • 34547572235 scopus 로고    scopus 로고
    • CdpNPT, an N-prenyltransferase from Aspergillus fumigatus: Overproduction, purification and biochemical characterisation
    • DOI 10.1002/cbic.200700079
    • 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 (Pubitemid 47194823)
    • (2007) ChemBioChem , vol.8 , Issue.10 , pp. 1154-1161
    • Yin, W.-B.1    Ruan, H.-L.2    Westrich, L.3    Grundmann, A.4    Li, S.-M.5
  • 49
    • 67249153458 scopus 로고    scopus 로고
    • Stereospecific synthesis of aszonalenins by using two recombinant prenyltransferases
    • W-B Yin J Cheng S-M Li 2009 Stereospecific synthesis of aszonalenins by using two recombinant prenyltransferases Org Biomol Chem 7 2202 2207
    • (2009) Org Biomol Chem , vol.7 , pp. 2202-2207
    • Yin, W.-B.1    Cheng, J.2    Li, S.-M.3
  • 50
    • 58649098990 scopus 로고    scopus 로고
    • Acetylaszonalenin biosynthesis in Neosartorya fischeri: Identification of the biosynthetic gene cluster by genomic mining and functional proof of the genes by biochemical investigation
    • 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
    • (2009) J Biol Chem , vol.284 , pp. 100-109
    • Yin, W.-B.1    Grundmann, A.2    Cheng, J.3    Li, S.-M.4
  • 52
    • 3042553356 scopus 로고    scopus 로고
    • Fumigaclavine C improves concanavalin A-induced liver injury in mice mainly via inhibiting TNF-alpha production and lymphocyte adhesion to extracellular matrices
    • Y Zhao J Liu J Wang L Wang H Yin R Tan Q Xu 2004 Fumigaclavine C improves concanavalin A-induced liver injury in mice mainly via inhibiting TNF-alpha production and lymphocyte adhesion to extracellular matrices J Pharm Pharmacol 56 775 782
    • (2004) J Pharm Pharmacol , vol.56 , pp. 775-782
    • Zhao, Y.1    Liu, J.2    Wang, J.3    Wang, L.4    Yin, H.5    Tan, R.6    Xu, Q.7
  • 53
    • 60549099609 scopus 로고    scopus 로고
    • Substrate promiscuity of the cyclic dipeptide prenyltransferases from Aspergillus fumigatus
    • H Zou X Zheng S-M Li 2009 Substrate promiscuity of the cyclic dipeptide prenyltransferases from Aspergillus fumigatus J Nat Prod 72 44 52
    • (2009) J Nat Prod , vol.72 , pp. 44-52
    • Zou, H.1    Zheng, X.2    Li, S.-M.3


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