메뉴 건너뛰기




Volumn 20, Issue 6, 2013, Pages 796-805

Unconventional origin and hybrid system for construction of pyrrolopyrrole moiety in kosinostatin biosynthesis

Author keywords

[No Author keywords available]

Indexed keywords

AMIDINE; ANTINEOPLASTIC ANTIBIOTIC; KOSINOSTATIN; NICOTINIC ACID; POLYKETIDE SYNTHASE; PYRROLE DERIVATIVE; PYRROLOPYRROLE; RIBOSE; TRYPTOPHAN; UNCLASSIFIED DRUG;

EID: 84879359984     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2013.04.013     Document Type: Article
Times cited : (27)

References (45)
  • 1
    • 77956600082 scopus 로고    scopus 로고
    • Characterization of glycosyltransferase DesVII and its auxiliary partner protein DesVIII in the methymycin/picromycin biosynthetic pathway
    • S.A. Borisova, and H.-W. Liu Characterization of glycosyltransferase DesVII and its auxiliary partner protein DesVIII in the methymycin/picromycin biosynthetic pathway Biochemistry 49 2010 8071 8084
    • (2010) Biochemistry , vol.49 , pp. 8071-8084
    • Borisova, S.A.1    Liu, H.-W.2
  • 2
    • 79952602234 scopus 로고    scopus 로고
    • The imidato-alkenyllithium route for the synthesis of the isoquinocycline-pyrrolopyrrole substructure
    • M.A. Breuning, K. Harms, and U. Koert The imidato-alkenyllithium route for the synthesis of the isoquinocycline-pyrrolopyrrole substructure Org. Lett. 13 2011 1402 1405
    • (2011) Org. Lett. , vol.13 , pp. 1402-1405
    • Breuning, M.A.1    Harms, K.2    Koert, U.3
  • 3
    • 0034013269 scopus 로고    scopus 로고
    • Predictive, structure-based model of amino acid recognition by nonribosomal peptide synthetase adenylation domains
    • G.L. Challis, J. Ravel, and C.A. Townsend Predictive, structure-based model of amino acid recognition by nonribosomal peptide synthetase adenylation domains Chem. Biol. 7 2000 211 224
    • (2000) Chem. Biol. , vol.7 , pp. 211-224
    • Challis, G.L.1    Ravel, J.2    Townsend, C.A.3
  • 4
    • 0032545041 scopus 로고    scopus 로고
    • Biosynthesis of yersiniose: Attachment of the two-carbon branched-chain is catalyzed by a thiamine pyrophosphate-dependent flavoprotein
    • H. Chen, Z. Guo, and H.-W. Liu Biosynthesis of yersiniose: attachment of the two-carbon branched-chain is catalyzed by a thiamine pyrophosphate-dependent flavoprotein J. Am. Chem. Soc. 120 1998 11796 11797
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11796-11797
    • Chen, H.1    Guo, Z.2    Liu, H.-W.3
  • 7
    • 0036843634 scopus 로고    scopus 로고
    • Expression, purification, and characterization of AknX anthrone oxygenase, which is involved in aklavinone biosynthesis in Streptomyces galilaeus
    • J.-Y. Chung, I. Fujii, S. Harada, U. Sankawa, and Y. Ebizuka Expression, purification, and characterization of AknX anthrone oxygenase, which is involved in aklavinone biosynthesis in Streptomyces galilaeus J. Bacteriol. 184 2002 6115 6122
    • (2002) J. Bacteriol. , vol.184 , pp. 6115-6122
    • Chung, J.-Y.1    Fujii, I.2    Harada, S.3    Sankawa, U.4    Ebizuka, Y.5
  • 8
    • 77956204125 scopus 로고    scopus 로고
    • Synthesis of the isoquinocycline-pyrrolopyrrole substructure
    • J. Cordes, K. Harms, and U. Koert Synthesis of the isoquinocycline- pyrrolopyrrole substructure Org. Lett. 12 2010 3808 3811
    • (2010) Org. Lett. , vol.12 , pp. 3808-3811
    • Cordes, J.1    Harms, K.2    Koert, U.3
  • 9
    • 66149105072 scopus 로고    scopus 로고
    • Biosynthesis of aromatic polyketides in bacteria
    • A. Das, and C. Khosla Biosynthesis of aromatic polyketides in bacteria Acc. Chem. Res. 42 2009 631 639
    • (2009) Acc. Chem. Res. , vol.42 , pp. 631-639
    • Das, A.1    Khosla, C.2
  • 10
    • 34447128741 scopus 로고    scopus 로고
    • Kosinostatin, a major secondary metabolite isolated from the culture filtrate of Streptomyces violaceusniger strain HAL64
    • M.Y. El-Naggar Kosinostatin, a major secondary metabolite isolated from the culture filtrate of Streptomyces violaceusniger strain HAL64 J. Microbiol. 45 2007 262 267
    • (2007) J. Microbiol. , vol.45 , pp. 262-267
    • El-Naggar, M.Y.1
  • 11
    • 46049113897 scopus 로고    scopus 로고
    • Orchestration of discoid polyketide cyclization in the resistomycin pathway
    • K. Fritzsche, K. Ishida, and C. Hertweck Orchestration of discoid polyketide cyclization in the resistomycin pathway J. Am. Chem. Soc. 130 2008 8307 8316
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8307-8316
    • Fritzsche, K.1    Ishida, K.2    Hertweck, C.3
  • 12
    • 0036203948 scopus 로고    scopus 로고
    • Kosinostatin, a quinocycline antibiotic with antitumor activity from Micromonospora sp. TP-A0468
    • T. Furumai, Y. Igarashi, H. Higuchi, N. Saito, and T. Oki Kosinostatin, a quinocycline antibiotic with antitumor activity from Micromonospora sp. TP-A0468 J. Antibiot. (Tokyo) 55 2002 128 133
    • (2002) J. Antibiot. (Tokyo) , vol.55 , pp. 128-133
    • Furumai, T.1    Igarashi, Y.2    Higuchi, H.3    Saito, N.4    Oki, T.5
  • 13
    • 33745143939 scopus 로고    scopus 로고
    • Isolation, characterization, and heterologous expression of the biosynthesis gene cluster for the antitumor anthracycline steffimycin
    • S. Gullón, C. Olano, M.S. Abdelfattah, A.F. Braña, J. Rohr, C. Méndez, and J.A. Salas Isolation, characterization, and heterologous expression of the biosynthesis gene cluster for the antitumor anthracycline steffimycin Appl. Environ. Microbiol. 72 2006 4172 4183
    • (2006) Appl. Environ. Microbiol. , vol.72 , pp. 4172-4183
    • Gullón, S.1    Olano, C.2    Abdelfattah, M.S.3    Braña, A.F.4    Rohr, J.5    Méndez, C.6    Salas, J.A.7
  • 14
    • 33846923183 scopus 로고    scopus 로고
    • Type II polyketide synthases: Gaining a deeper insight into enzymatic teamwork
    • C. Hertweck, A. Luzhetskyy, Y. Rebets, and A. Bechthold Type II polyketide synthases: gaining a deeper insight into enzymatic teamwork Nat. Prod. Rep. 24 2007 162 190
    • (2007) Nat. Prod. Rep. , vol.24 , pp. 162-190
    • Hertweck, C.1    Luzhetskyy, A.2    Rebets, Y.3    Bechthold, A.4
  • 15
    • 0036211642 scopus 로고    scopus 로고
    • NMR analysis of quinocycline antibiotics: Structure determination of kosinostatin, an antitumor substance from Micromonospora sp. TP-A0468
    • Y. Igarashi, H. Higuchi, T. Oki, and T. Furumai NMR analysis of quinocycline antibiotics: structure determination of kosinostatin, an antitumor substance from Micromonospora sp. TP-A0468 J. Antibiot. (Tokyo) 55 2002 134 140
    • (2002) J. Antibiot. (Tokyo) , vol.55 , pp. 134-140
    • Igarashi, Y.1    Higuchi, H.2    Oki, T.3    Furumai, T.4
  • 16
    • 77957276543 scopus 로고    scopus 로고
    • Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases
    • T. Itoh, K. Tokunaga, Y. Matsuda, I. Fujii, I. Abe, Y. Ebizuka, and T. Kushiro Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases Nat. Chem. 2 2010 858 864
    • (2010) Nat. Chem. , vol.2 , pp. 858-864
    • Itoh, T.1    Tokunaga, K.2    Matsuda, Y.3    Fujii, I.4    Abe, I.5    Ebizuka, Y.6    Kushiro, T.7
  • 17
    • 32244443360 scopus 로고    scopus 로고
    • Priming type II polyketide synthases via a type II nonribosomal peptide synthetase mechanism
    • M. Izumikawa, Q. Cheng, and B.S. Moore Priming type II polyketide synthases via a type II nonribosomal peptide synthetase mechanism J. Am. Chem. Soc. 128 2006 1428 1429
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 1428-1429
    • Izumikawa, M.1    Cheng, Q.2    Moore, B.S.3
  • 19
    • 36148946687 scopus 로고    scopus 로고
    • Tryptophan biosynthesis in stramenopiles: Eukaryotic winners in the diatom complex chloroplast
    • K. Jiroutová, A. Horák, C. Bowler, and M. Oborník Tryptophan biosynthesis in stramenopiles: eukaryotic winners in the diatom complex chloroplast J. Mol. Evol. 65 2007 496 511
    • (2007) J. Mol. Evol. , vol.65 , pp. 496-511
    • Jiroutová, K.1    Horák, A.2    Bowler, C.3    Oborník, M.4
  • 21
    • 84859633326 scopus 로고    scopus 로고
    • Delineation of gilvocarcin, jadomycin, and landomycin pathways through combinatorial biosynthetic enzymology
    • M.K. Kharel, and J. Rohr Delineation of gilvocarcin, jadomycin, and landomycin pathways through combinatorial biosynthetic enzymology Curr. Opin. Chem. Biol. 16 2012 150 161
    • (2012) Curr. Opin. Chem. Biol. , vol.16 , pp. 150-161
    • Kharel, M.K.1    Rohr, J.2
  • 22
    • 36348983413 scopus 로고    scopus 로고
    • Stereoselective synthesis of methyl 7-dihydro-trioxacarcinoside B
    • C.M. König, K. Harms, and U. Koert Stereoselective synthesis of methyl 7-dihydro-trioxacarcinoside B Org. Lett. 9 2007 4777 4779
    • (2007) Org. Lett. , vol.9 , pp. 4777-4779
    • König, C.M.1    Harms, K.2    Koert, U.3
  • 23
    • 34547662949 scopus 로고    scopus 로고
    • Biosynthesis of pentangular polyphenols: Deductions from the benastatin and griseorhodin pathways
    • G. Lackner, A. Schenk, Z. Xu, K. Reinhardt, Z.S. Yunt, J. Piel, and C. Hertweck Biosynthesis of pentangular polyphenols: deductions from the benastatin and griseorhodin pathways J. Am. Chem. Soc. 129 2007 9306 9312
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 9306-9312
    • Lackner, G.1    Schenk, A.2    Xu, Z.3    Reinhardt, K.4    Yunt, Z.S.5    Piel, J.6    Hertweck, C.7
  • 25
    • 34548214188 scopus 로고    scopus 로고
    • Characterization of rhodosaminyl transfer by the AknS/AknT glycosylation complex and its use in reconstituting the biosynthetic pathway of aclacinomycin A
    • C. Leimkuhler, M. Fridman, T. Lupoli, S. Walker, C.T. Walsh, and D. Kahne Characterization of rhodosaminyl transfer by the AknS/AknT glycosylation complex and its use in reconstituting the biosynthetic pathway of aclacinomycin A J. Am. Chem. Soc. 129 2007 10546 10550
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 10546-10550
    • Leimkuhler, C.1    Fridman, M.2    Lupoli, T.3    Walker, S.4    Walsh, C.T.5    Kahne, D.6
  • 26
    • 0015515035 scopus 로고
    • Studies on the biosynthesis of the branched-chain sugars from the quinocycline complex
    • U. Matern, and H. Grisebach Studies on the biosynthesis of the branched-chain sugars from the quinocycline complex Eur. J. Biochem. 29 1972 5 11
    • (1972) Eur. J. Biochem. , vol.29 , pp. 5-11
    • Matern, U.1    Grisebach, H.2
  • 28
    • 72449196714 scopus 로고    scopus 로고
    • Biosynthetic studies of aziridine formation in azicemicins
    • Y. Ogasawara, and H.-W. Liu Biosynthetic studies of aziridine formation in azicemicins J. Am. Chem. Soc. 131 2009 18066 18068
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 18066-18068
    • Ogasawara, Y.1    Liu, H.-W.2
  • 29
    • 77950127253 scopus 로고    scopus 로고
    • Post-PKS tailoring steps in natural product-producing actinomycetes from the perspective of combinatorial biosynthesis
    • C. Olano, C. Méndez, and J.A. Salas Post-PKS tailoring steps in natural product-producing actinomycetes from the perspective of combinatorial biosynthesis Nat. Prod. Rep. 27 2010 571 616
    • (2010) Nat. Prod. Rep. , vol.27 , pp. 571-616
    • Olano, C.1    Méndez, C.2    Salas, J.A.3
  • 30
    • 84856179567 scopus 로고    scopus 로고
    • Enzymatic total synthesis of defucogilvocarcin M and its implications for gilvocarcin biosynthesis
    • P. Pahari, M.K. Kharel, M.D. Shepherd, S.G. van Lanen, and J. Rohr Enzymatic total synthesis of defucogilvocarcin M and its implications for gilvocarcin biosynthesis Angew. Chem. Int. Ed. Engl. 51 2012 1216 1220
    • (2012) Angew. Chem. Int. Ed. Engl. , vol.51 , pp. 1216-1220
    • Pahari, P.1    Kharel, M.K.2    Shepherd, M.D.3    Van Lanen, S.G.4    Rohr, J.5
  • 31
    • 29144439151 scopus 로고    scopus 로고
    • Characterization of the ectoine biosynthesis genes of haloalkalotolerant obligate methanotroph "methylomicrobium alcaliphilum 20Z"
    • A.S. Reshetnikov, V.N. Khmelenina, and Y.A. Trotsenko Characterization of the ectoine biosynthesis genes of haloalkalotolerant obligate methanotroph "Methylomicrobium alcaliphilum 20Z" Arch. Microbiol. 184 2006 286 297
    • (2006) Arch. Microbiol. , vol.184 , pp. 286-297
    • Reshetnikov, A.S.1    Khmelenina, V.N.2    Trotsenko, Y.A.3
  • 33
    • 84861601448 scopus 로고    scopus 로고
    • Discovery of a two-component monooxygenase SnoaW/SnoaL2 involved in nogalamycin biosynthesis
    • V. Siitonen, B. Blauenburg, P. Kallio, P. Mäntsälä, and M. Metsä-Ketelä Discovery of a two-component monooxygenase SnoaW/SnoaL2 involved in nogalamycin biosynthesis Chem. Biol. 19 2012 638 646
    • (2012) Chem. Biol. , vol.19 , pp. 638-646
    • Siitonen, V.1    Blauenburg, B.2    Kallio, P.3    Mäntsälä, P.4    Metsä-Ketelä, M.5
  • 34
    • 0033179468 scopus 로고    scopus 로고
    • The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases
    • T. Stachelhaus, H.D. Mootz, and M.A. Marahiel The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases Chem. Biol. 6 1999 493 505
    • (1999) Chem. Biol. , vol.6 , pp. 493-505
    • Stachelhaus, T.1    Mootz, H.D.2    Marahiel, M.A.3
  • 35
    • 0033955088 scopus 로고    scopus 로고
    • Identification of a cyclase gene dictating the C-9 stereochemistry of anthracyclines from Streptomyces nogalater
    • S. Torkkell, T. Kunnari, K. Palmu, J. Hakala, P. Mäntsälä, and K. Ylihonko Identification of a cyclase gene dictating the C-9 stereochemistry of anthracyclines from Streptomyces nogalater Antimicrob. Agents Chemother. 44 2000 396 399
    • (2000) Antimicrob. Agents Chemother. , vol.44 , pp. 396-399
    • Torkkell, S.1    Kunnari, T.2    Palmu, K.3    Hakala, J.4    Mäntsälä, P.5    Ylihonko, K.6
  • 36
    • 0142135988 scopus 로고    scopus 로고
    • Polyketide chain length control by chain length factor
    • Y. Tang, S.-C. Tsai, and C. Khosla Polyketide chain length control by chain length factor J. Am. Chem. Soc. 125 2003 12708 12709
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12708-12709
    • Tang, Y.1    Tsai, S.-C.2    Khosla, C.3
  • 38
    • 0035802125 scopus 로고    scopus 로고
    • A biosynthetic classification of fungal and streptomycete fused-ring aromatic polyketides
    • R.A. Thomas A biosynthetic classification of fungal and streptomycete fused-ring aromatic polyketides ChemBioChem 2 2001 612 627
    • (2001) ChemBioChem , vol.2 , pp. 612-627
    • Thomas, R.A.1
  • 39
    • 12244281838 scopus 로고    scopus 로고
    • Genes involved in formation and attachment of a two-carbon chain as a component of eurekanate, a branched-chain sugar moiety of avilamycin A
    • I. Treede, G. Hauser, A. Mühlenweg, C. Hofmann, M. Schmidt, G. Weitnauer, S. Glaser, and A. Bechthold Genes involved in formation and attachment of a two-carbon chain as a component of eurekanate, a branched-chain sugar moiety of avilamycin A Appl. Environ. Microbiol. 71 2005 400 406
    • (2005) Appl. Environ. Microbiol. , vol.71 , pp. 400-406
    • Treede, I.1    Hauser, G.2    Mühlenweg, A.3    Hofmann, C.4    Schmidt, M.5    Weitnauer, G.6    Glaser, S.7    Bechthold, A.8
  • 40
    • 0001455712 scopus 로고
    • The structure of isoquinocycline A. An X-ray crystallographic determination
    • A. Tulinsky The structure of isoquinocycline A. An X-ray crystallographic determination J. Am. Chem. Soc. 86 1964 5368
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 5368
    • Tulinsky, A.1
  • 41
    • 44849143455 scopus 로고    scopus 로고
    • Mechanism and regulation of the Two-component FMN-dependent monooxygenase ActVA-ActVB from Streptomyces coelicolor
    • J. Valton, C. Mathevon, M. Fontecave, V. Nivière, and D.P. Ballou Mechanism and regulation of the Two-component FMN-dependent monooxygenase ActVA-ActVB from Streptomyces coelicolor J. Biol. Chem. 283 2008 10287 10296
    • (2008) J. Biol. Chem. , vol.283 , pp. 10287-10296
    • Valton, J.1    Mathevon, C.2    Fontecave, M.3    Nivière, V.4    Ballou, D.P.5
  • 42
    • 33746608987 scopus 로고    scopus 로고
    • Biological formation of pyrroles: Nature's logic and enzymatic machinery
    • C.T. Walsh, S. Garneau-Tsodikova, and A.R. Howard-Jones Biological formation of pyrroles: nature's logic and enzymatic machinery Nat. Prod. Rep. 23 2006 517 531
    • (2006) Nat. Prod. Rep. , vol.23 , pp. 517-531
    • Walsh, C.T.1    Garneau-Tsodikova, S.2    Howard-Jones, A.R.3
  • 43
    • 19544376849 scopus 로고    scopus 로고
    • Biosynthesis of the antitumor agent chartreusin involves the oxidative rearrangement of an anthracyclic polyketide
    • Z. Xu, K. Jakobi, K. Welzel, and C. Hertweck Biosynthesis of the antitumor agent chartreusin involves the oxidative rearrangement of an anthracyclic polyketide Chem. Biol. 12 2005 579 588
    • (2005) Chem. Biol. , vol.12 , pp. 579-588
    • Xu, Z.1    Jakobi, K.2    Welzel, K.3    Hertweck, C.4
  • 44
    • 38649121769 scopus 로고    scopus 로고
    • Biosynthetic investigations of lactonamycin and lactonamycin z: Cloning of the biosynthetic gene clusters and discovery of an unusual starter unit
    • X. Zhang, L.B. Alemany, H.P. Fiedler, M. Goodfellow, and R.J. Parry Biosynthetic investigations of lactonamycin and lactonamycin z: cloning of the biosynthetic gene clusters and discovery of an unusual starter unit Antimicrob. Agents Chemother. 52 2008 574 585
    • (2008) Antimicrob. Agents Chemother. , vol.52 , pp. 574-585
    • Zhang, X.1    Alemany, L.B.2    Fiedler, H.P.3    Goodfellow, M.4    Parry, R.J.5
  • 45
    • 77953035258 scopus 로고    scopus 로고
    • Cyclization of aromatic polyketides from bacteria and fungi
    • H. Zhou, Y. Li, and Y. Tang Cyclization of aromatic polyketides from bacteria and fungi Nat. Prod. Rep. 27 2010 839 868
    • (2010) Nat. Prod. Rep. , vol.27 , pp. 839-868
    • Zhou, H.1    Li, Y.2    Tang, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.