메뉴 건너뛰기




Volumn 52, Issue 31, 2013, Pages 5217-5224

Predictive model for epoxide hydrolase-generated stereochemistry in the biosynthesis of nine-membered enediyne antitumor antibiotics

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUMOR ANTIBIOTICS; DOUBLE MUTATION; EPOXIDE HYDROLASES; GENOME MINING; PHYLOGENETIC ANALYSIS; PREDICTIVE MODELS; STREPTOMYCES GRISEUS; VICINAL DIOLS;

EID: 84881238218     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi400572a     Document Type: Article
Times cited : (6)

References (30)
  • 1
    • 27544456830 scopus 로고    scopus 로고
    • The impact of bacterial genomics on natural product research
    • Bode, H. B. and Müller, R. (2005) The impact of bacterial genomics on natural product research Angew. Chem., Int. Ed. 44, 6828-6846
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6828-6846
    • Bode, H.B.1    Müller, R.2
  • 3
    • 77649305354 scopus 로고    scopus 로고
    • Natural products version 2.0: Connecting genes to molecules
    • Walsh, C. T. and Fischbach, M. A. (2010) Natural products version 2.0: connecting genes to molecules J. Am. Chem. Soc. 132, 2469-2493
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 2469-2493
    • Walsh, C.T.1    Fischbach, M.A.2
  • 4
    • 0033528659 scopus 로고    scopus 로고
    • Unexpected divergence of enzyme function and sequence: "n-acylamino acid racemase" is o-succinylbenzoate synthase
    • Palmer, D. R. J., Garrett, J. B., Sharma, V., Meganathan, R., Babbitt, P. C., and Gerlt, J. A. (1999) Unexpected divergence of enzyme function and sequence: "N-acylamino acid racemase" is o-succinylbenzoate synthase Biochemistry 38, 4252-4258
    • (1999) Biochemistry , vol.38 , pp. 4252-4258
    • Palmer, D.R.J.1    Garrett, J.B.2    Sharma, V.3    Meganathan, R.4    Babbitt, P.C.5    Gerlt, J.A.6
  • 5
    • 38649097499 scopus 로고    scopus 로고
    • Biosynthesis of the enediyne antitumor antibiotic C-1027 involves a new branching point in chorismate metabolism
    • Van Lanen, S. G., Lin, S., and Shen, B. (2008) Biosynthesis of the enediyne antitumor antibiotic C-1027 involves a new branching point in chorismate metabolism Proc. Natl. Acad. Sci. U.S.A. 105, 494-499
    • (2008) Proc. Natl. Acad. Sci. U.S.A. , vol.105 , pp. 494-499
    • Van Lanen, S.G.1    Lin, S.2    Shen, B.3
  • 7
    • 0035291191 scopus 로고    scopus 로고
    • SMANCS and polymer-conjugated macromolecular drugs: Advantages in cancer chemotherapy
    • Maeda, H. (2001) SMANCS and polymer-conjugated macromolecular drugs: advantages in cancer chemotherapy Adv. Drug Delivery Rev. 46, 169-185
    • (2001) Adv. Drug Delivery Rev. , vol.46 , pp. 169-185
    • Maeda, H.1
  • 8
    • 0026045597 scopus 로고
    • Chemistry and biology of the enediyne anticancer antibiotics
    • Nicolaou, K. C. and Dai, W. M. (1991) Chemistry and biology of the enediyne anticancer antibiotics Angew. Chem., Int. Ed. Engl. 30, 1387-1416
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 1387-1416
    • Nicolaou, K.C.1    Dai, W.M.2
  • 9
    • 0034753903 scopus 로고    scopus 로고
    • Mylotarg: Antibody-targeted chemotherapy comes of age
    • Sievers, E. L. and Linenberger, M. (2001) Mylotarg: antibody-targeted chemotherapy comes of age Curr. Opin. Oncol. 13, 522-527
    • (2001) Curr. Opin. Oncol. , vol.13 , pp. 522-527
    • Sievers, E.L.1    Linenberger, M.2
  • 10
    • 41549124102 scopus 로고    scopus 로고
    • The biosynthetic genes encoding for the production of the dynemicin enediyne core in Micromonospora chersina ATCC53710
    • Gao, Q. and Thorson, J. S. (2008) The biosynthetic genes encoding for the production of the dynemicin enediyne core in Micromonospora chersina ATCC53710 FEMS Microbiol. Lett. 282, 105-114
    • (2008) FEMS Microbiol. Lett. , vol.282 , pp. 105-114
    • Gao, Q.1    Thorson, J.S.2
  • 12
    • 0347721776 scopus 로고    scopus 로고
    • Biosynthesis of the enediyne antitumor antibiotic C-1027
    • Liu, W., Christenson, S. D., Standage, S., and Shen, B. (2002) Biosynthesis of the enediyne antitumor antibiotic C-1027 Science 297, 1170-1173
    • (2002) Science , vol.297 , pp. 1170-1173
    • Liu, W.1    Christenson, S.D.2    Standage, S.3    Shen, B.4
  • 13
    • 20144363202 scopus 로고    scopus 로고
    • The neocarzinostatin biosynthetic gene cluster from Streptomyces carzinostaticus ATCC 15944 involving two iterative type i polyketide synthases
    • Liu, W., Nonaka, K., Nie, L., Zhang, J., Christenson, S. D., Bae, J., Van Lanen, S. G., Zazopoulos, E., Farnet, C. M., Yang, C. F., and Shen, B. (2005) The neocarzinostatin biosynthetic gene cluster from Streptomyces carzinostaticus ATCC 15944 involving two iterative type I polyketide synthases Chem. Biol. 12, 293-302
    • (2005) Chem. Biol. , vol.12 , pp. 293-302
    • Liu, W.1    Nonaka, K.2    Nie, L.3    Zhang, J.4    Christenson, S.D.5    Bae, J.6    Van Lanen, S.G.7    Zazopoulos, E.8    Farnet, C.M.9    Yang, C.F.10    Shen, B.11
  • 14
    • 35848971002 scopus 로고    scopus 로고
    • Characterization of the maduropeptin biosynthetic gene cluster from Actinomadura madurae ATCC 39144 supporting a unifying paradigm for enediyne biosynthesis
    • Van Lanen, S. G., Oh, T.-J., Liu, W., Wendt-Pienkowski, E., and Shen, B. (2007) Characterization of the maduropeptin biosynthetic gene cluster from Actinomadura madurae ATCC 39144 supporting a unifying paradigm for enediyne biosynthesis J. Am. Chem. Soc. 129, 13082-13094
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 13082-13094
    • Van Lanen, S.G.1    Oh, T.-J.2    Liu, W.3    Wendt-Pienkowski, E.4    Shen, B.5
  • 15
    • 77950109576 scopus 로고    scopus 로고
    • Complexity and simplicity in the biosynthesis of enediyne natural products
    • Liang, Z.-X. (2010) Complexity and simplicity in the biosynthesis of enediyne natural products Nat. Prod. Rep. 27, 499-528
    • (2010) Nat. Prod. Rep. , vol.27 , pp. 499-528
    • Liang, Z.-X.1
  • 16
    • 44649201476 scopus 로고    scopus 로고
    • Biosynthesis of enediyne antitumor antibiotics
    • Van Lanen, S. G. and Shen, B. (2008) Biosynthesis of enediyne antitumor antibiotics Curr. Top. Med. Chem. 8, 448-459
    • (2008) Curr. Top. Med. Chem. , vol.8 , pp. 448-459
    • Van Lanen, S.G.1    Shen, B.2
  • 17
    • 77954937819 scopus 로고    scopus 로고
    • Polyketide synthase chemistry does not direct biosynthetic divergence between 9- and 10-membered enediynes
    • Horsman, G. P., Chen, Y., Thorson, J. S., and Shen, B. (2010) Polyketide synthase chemistry does not direct biosynthetic divergence between 9- and 10-membered enediynes Proc. Natl. Acad. Sci. U.S.A. 107, 11331-11335
    • (2010) Proc. Natl. Acad. Sci. U.S.A. , vol.107 , pp. 11331-11335
    • Horsman, G.P.1    Chen, Y.2    Thorson, J.S.3    Shen, B.4
  • 18
    • 0142027815 scopus 로고    scopus 로고
    • Rapid PCR amplification of minimal enediyne polyketide synthase cassettes leads to a predictive familial classification model
    • Liu, W., Ahlert, J., Gao, Q., Wendt-Pienkowski, E., Shen, B., and Thorson, J. S. (2003) Rapid PCR amplification of minimal enediyne polyketide synthase cassettes leads to a predictive familial classification model Proc. Natl. Acad. Sci. U.S.A. 100, 11959-11963
    • (2003) Proc. Natl. Acad. Sci. U.S.A. , vol.100 , pp. 11959-11963
    • Liu, W.1    Ahlert, J.2    Gao, Q.3    Wendt-Pienkowski, E.4    Shen, B.5    Thorson, J.S.6
  • 19
    • 70450280711 scopus 로고    scopus 로고
    • Characterization of the SgcF epoxide hydrolase supporting an (R)-vicinal diol intermediate for enediyne antitumor antibiotic C-1027 biosynthesis
    • Lin, S., Horsman, G. P., Chen, Y., Li, W., and Shen, B. (2009) Characterization of the SgcF epoxide hydrolase supporting an (R)-vicinal diol intermediate for enediyne antitumor antibiotic C-1027 biosynthesis J. Am. Chem. Soc. 131, 16410-16417
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 16410-16417
    • Lin, S.1    Horsman, G.P.2    Chen, Y.3    Li, W.4    Shen, B.5
  • 20
    • 77956192684 scopus 로고    scopus 로고
    • Characterization of the epoxide hydrolase NcsF2 from the neocarzinostatin biosynthetic gene cluster
    • Lin, S., Horsman, G. P., and Shen, B. (2010) Characterization of the epoxide hydrolase NcsF2 from the neocarzinostatin biosynthetic gene cluster Org. Lett. 12, 3816-3819
    • (2010) Org. Lett. , vol.12 , pp. 3816-3819
    • Lin, S.1    Horsman, G.P.2    Shen, B.3
  • 21
    • 84875860289 scopus 로고    scopus 로고
    • Cloning and sequencing of the kedarcidin biosynthetic gene cluster from Streptoalloteichus sp. ATCC 53650 revealing new insights into biosynthesis of the enediyne family of antitumor antibiotics
    • Lohman, J. R., Huang, S.-X., Horsman, G. P., Dilfer, P. E., Huang, T., Chen, Y., Wendt-Pienkowski, E., and Shen, B. (2013) Cloning and sequencing of the kedarcidin biosynthetic gene cluster from Streptoalloteichus sp. ATCC 53650 revealing new insights into biosynthesis of the enediyne family of antitumor antibiotics Mol. BioSyst. 9, 478-491
    • (2013) Mol. BioSyst. , vol.9 , pp. 478-491
    • Lohman, J.R.1    Huang, S.-X.2    Horsman, G.P.3    Dilfer, P.E.4    Huang, T.5    Chen, Y.6    Wendt-Pienkowski, E.7    Shen, B.8
  • 24
    • 84876533617 scopus 로고    scopus 로고
    • Building phylogenetic trees from molecular data with MEGA
    • Hall, B. G. (2013) Building phylogenetic trees from molecular data with MEGA Mol. Biol. Evol. 30, 1229-1235
    • (2013) Mol. Biol. Evol. , vol.30 , pp. 1229-1235
    • Hall, B.G.1
  • 26
    • 33646084392 scopus 로고    scopus 로고
    • Diversity and biocatalytic potential of epoxide hydrolases identified by genome analysis
    • van Loo, B., Kingma, J., Arand, M., Wubbolts, M. G., and Janssen, D. B. (2006) Diversity and biocatalytic potential of epoxide hydrolases identified by genome analysis Appl. Environ. Microbiol. 72, 2905-2917
    • (2006) Appl. Environ. Microbiol. , vol.72 , pp. 2905-2917
    • Van Loo, B.1    Kingma, J.2    Arand, M.3    Wubbolts, M.G.4    Janssen, D.B.5
  • 27
    • 1942517067 scopus 로고    scopus 로고
    • Reaction mechanism of soluble epoxide hydrolase: Insights from molecular dynamics simulations
    • Schiøtt, B. and Bruice, T. C. (2002) Reaction mechanism of soluble epoxide hydrolase: insights from molecular dynamics simulations J. Am. Chem. Soc. 124, 14558-14570
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 14558-14570
    • Schiøtt, B.1    Bruice, T.C.2
  • 28
    • 39749100521 scopus 로고    scopus 로고
    • Unraveling the biosynthesis of the sporolide cyclohexenone building block
    • McGlinchey, R. P., Nett, M., and Moore, B. S. (2008) Unraveling the biosynthesis of the sporolide cyclohexenone building block J. Am. Chem. Soc. 130, 2406-2407
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 2406-2407
    • McGlinchey, R.P.1    Nett, M.2    Moore, B.S.3
  • 29
    • 33645038629 scopus 로고    scopus 로고
    • Do the terms "% ee" and "% de" make sense as expressions of stereoisomer composition or stereoselectivity?
    • Gawley, R. E. (2006) Do the terms "% ee" and "% de" make sense as expressions of stereoisomer composition or stereoselectivity? J. Org. Chem. 71, 2411-2416
    • (2006) J. Org. Chem. , vol.71 , pp. 2411-2416
    • Gawley, R.E.1
  • 30
    • 77049095558 scopus 로고    scopus 로고
    • Mutations in salt-bridging residues at the interface of the core and lid domains of epoxide hydrolase StEH1 affect regioselectivity, protein stability and hysteresis
    • Lindberg, D., Ahmad, S., and Widersten, M. (2010) Mutations in salt-bridging residues at the interface of the core and lid domains of epoxide hydrolase StEH1 affect regioselectivity, protein stability and hysteresis Arch. Biochem. Biophys. 495, 165-173
    • (2010) Arch. Biochem. Biophys. , vol.495 , pp. 165
    • Lindberg, D.1    Ahmad, S.2    Widersten, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.