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Volumn 6, Issue 2, 2017, Pages 201-205

Engineering of Taxadiene Synthase for Improved Selectivity and Yield of a Key Taxol Biosynthetic Intermediate

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; PACLITAXEL; TERPENE; ISOMERASE; TAXA-4(5),11(12)-DIENE SYNTHASE;

EID: 85013188408     PISSN: None     EISSN: 21615063     Source Type: Journal    
DOI: 10.1021/acssynbio.6b00206     Document Type: Article
Times cited : (56)

References (22)
  • 4
    • 84926646130 scopus 로고    scopus 로고
    • Distributing a metabolic pathway among a microbial consortium enhances production of natural products
    • Zhou, K., Qiao, K., Edgar, S., and Stephanopoulos, G. (2015) Distributing a metabolic pathway among a microbial consortium enhances production of natural products Nat. Biotechnol. 33, 377-383 10.1038/nbt.3095
    • (2015) Nat. Biotechnol. , vol.33 , pp. 377-383
    • Zhou, K.1    Qiao, K.2    Edgar, S.3    Stephanopoulos, G.4
  • 5
    • 44449085997 scopus 로고    scopus 로고
    • CYP725A4 from yew catalyzes complex structural rearrangement of taxa-4(5),11(12)-diene into the cyclic ether 5(12)-oxa-3(11)-cyclotaxane
    • Rontein, D., Onillon, S., Herbette, G., Lesot, A., Werck-Reichhart, D., Sallaud, C., and Tissier, A. (2008) CYP725A4 from yew catalyzes complex structural rearrangement of taxa-4(5),11(12)-diene into the cyclic ether 5(12)-oxa-3(11)-cyclotaxane J. Biol. Chem. 283, 6067-75 10.1074/jbc.M708950200
    • (2008) J. Biol. Chem. , vol.283 , pp. 6067-6075
    • Rontein, D.1    Onillon, S.2    Herbette, G.3    Lesot, A.4    Werck-Reichhart, D.5    Sallaud, C.6    Tissier, A.7
  • 6
    • 84966417264 scopus 로고    scopus 로고
    • Accessing low-oxidation state taxanes: Is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway?
    • Barton, N. a, Marsh, B. J., Lewis, W., Narraidoo, N., Seymour, G., Fray, R., and Hayes, C. J. (2016) Accessing low-oxidation state taxanes: Is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway? Chem. Sci. 00, 1-6 10.1039/C5SC03463A
    • (2016) Chem. Sci. , pp. 1-6
    • Barton, N.A.1    Marsh, B.J.2    Lewis, W.3    Narraidoo, N.4    Seymour, G.5    Fray, R.6    Hayes, C.J.7
  • 7
    • 84959378627 scopus 로고    scopus 로고
    • Mechanistic Insights into Taxadiene Epoxidation by Taxadiene-5α-Hydroxylase
    • Edgar, S., Zhou, K., Qiao, K., King, J. R., Simpson, J. H., and Stephanopoulos, G. (2016) Mechanistic Insights into Taxadiene Epoxidation by Taxadiene-5α-Hydroxylase ACS Chem. Biol. 11, 460 10.1021/acschembio.5b00767
    • (2016) ACS Chem. Biol. , vol.11 , pp. 460
    • Edgar, S.1    Zhou, K.2    Qiao, K.3    King, J.R.4    Simpson, J.H.5    Stephanopoulos, G.6
  • 8
    • 2642518854 scopus 로고    scopus 로고
    • Cytochrome P450 taxadiene 5-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis
    • Jennewein, S., Long, R. M., Williams, R. M., and Croteau, R. (2004) Cytochrome P450 taxadiene 5-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis Chem. Biol. 11, 379-387 10.1016/j.chembiol.2004.02.022
    • (2004) Chem. Biol. , vol.11 , pp. 379-387
    • Jennewein, S.1    Long, R.M.2    Williams, R.M.3    Croteau, R.4
  • 9
    • 84911886445 scopus 로고    scopus 로고
    • Journal of Molecular Catalysis B
    • Yadav, V. G. (2014) Journal of Molecular Catalysis B J. Mol. Catal. B: Enzym. 110, 154-164 10.1016/j.molcatb.2014.10.004
    • (2014) J. Mol. Catal. B: Enzym. , vol.110 , pp. 154-164
    • Yadav, V.G.1
  • 11
    • 0028964563 scopus 로고
    • Cyclization of geranylgeranyl diphosphate to taxa-4 (5), 11 (12)-diene is the committed step of taxol biosynthesis in Pacific yew
    • Koepp, A., Hezari, M., and Zajicek, J. (1995) Cyclization of geranylgeranyl diphosphate to taxa-4 (5), 11 (12)-diene is the committed step of taxol biosynthesis in Pacific yew J. Biol. Chem. 270, 8686 10.1074/jbc.270.15.8686
    • (1995) J. Biol. Chem. , vol.270 , pp. 8686
    • Koepp, A.1    Hezari, M.2    Zajicek, J.3
  • 12
    • 78650991785 scopus 로고    scopus 로고
    • Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis
    • Köksal, M., Jin, Y., Coates, R. M., Croteau, R., and Christianson, D. W. (2011) Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis Nature 469, 116-20 10.1038/nature09628
    • (2011) Nature , vol.469 , pp. 116-120
    • Köksal, M.1    Jin, Y.2    Coates, R.M.3    Croteau, R.4    Christianson, D.W.5
  • 13
    • 0029979356 scopus 로고    scopus 로고
    • Mechanism of taxadiene synthase, a diterpene cyclase that catalyzes the first step of taxol biosynthesis in Pacific yew
    • Lin, X., Hezari, M., Koepp, a. E., Floss, H. G., and Croteau, R. (1996) Mechanism of taxadiene synthase, a diterpene cyclase that catalyzes the first step of taxol biosynthesis in Pacific yew Biochemistry 35, 2968-77 10.1021/bi9526239
    • (1996) Biochemistry , vol.35 , pp. 2968-2977
    • Lin, X.1    Hezari, M.2    Koepp, A.E.3    Floss, H.G.4    Croteau, R.5
  • 14
    • 20344394434 scopus 로고    scopus 로고
    • Stereochemistry of the macrocyclization and elimination steps in taxadiene biosynthesis through deuterium labeling
    • Jin, Q., Williams, D. C., Hezari, M., Croteau, R., and Coates, R. M. (2005) Stereochemistry of the macrocyclization and elimination steps in taxadiene biosynthesis through deuterium labeling J. Org. Chem. 70, 4667-4675 10.1021/jo0502091
    • (2005) J. Org. Chem. , vol.70 , pp. 4667-4675
    • Jin, Q.1    Williams, D.C.2    Hezari, M.3    Croteau, R.4    Coates, R.M.5
  • 15
    • 29044448311 scopus 로고    scopus 로고
    • Verticillane Derivatives from Bursera suntui and Busera kerberi
    • Hernandez-Hernandez, J. and Roman-Marin, L. U. (2005) Verticillane Derivatives from Bursera suntui and Busera kerberi J. Nat. Prod. 68, 1598-1602 10.1021/np050323e
    • (2005) J. Nat. Prod. , vol.68 , pp. 1598-1602
    • Hernandez-Hernandez, J.1    Roman-Marin, L.U.2
  • 16
    • 27544462926 scopus 로고    scopus 로고
    • Taxoids occurring in the genus Taxus
    • CRC Press, Boca Raton, FL
    • Itokawa, H. (2003) Taxoids occurring in the genus Taxus. In Taxus: The Genus Taxus, CRC Press, Boca Raton, FL.
    • (2003) Taxus: The Genus Taxus
    • Itokawa, H.1
  • 17
    • 77953100438 scopus 로고    scopus 로고
    • What factors influence the rate constant of substrate epoxidation by compound i of cytochrome P450 and analogous iron(IV)-oxo oxidants?
    • Kumar, D., Karamzadeh, B., Sastry, G. N., and De Visser, S. P. (2010) What factors influence the rate constant of substrate epoxidation by compound i of cytochrome P450 and analogous iron(IV)-oxo oxidants? J. Am. Chem. Soc. 132, 7656-7667 10.1021/ja9106176
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 7656-7667
    • Kumar, D.1    Karamzadeh, B.2    Sastry, G.N.3    De Visser, S.P.4
  • 18
    • 26844530203 scopus 로고    scopus 로고
    • Catalytic mechanism of limonene epoxide hydrolase, a theoretical study
    • Hopmann, K. H., Hallberg, B. M., and Himo, F. (2005) Catalytic mechanism of limonene epoxide hydrolase, a theoretical study J. Am. Chem. Soc. 127, 14339-14347 10.1021/ja050940p
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 14339-14347
    • Hopmann, K.H.1    Hallberg, B.M.2    Himo, F.3
  • 19
    • 77957282147 scopus 로고    scopus 로고
    • Linalool dehydratase-isomerase, a bifunctional enzyme in the anaerobic degradation of monoterpenes
    • Brodkorb, D., Gottschall, M., Marmulla, R., Lüddeke, F., and Harder, J. (2010) Linalool dehydratase-isomerase, a bifunctional enzyme in the anaerobic degradation of monoterpenes J. Biol. Chem. 285, 30436-30442 10.1074/jbc.M109.084244
    • (2010) J. Biol. Chem. , vol.285 , pp. 30436-30442
    • Brodkorb, D.1    Gottschall, M.2    Marmulla, R.3    Lüddeke, F.4    Harder, J.5
  • 20
    • 84876981419 scopus 로고    scopus 로고
    • Deep sequencing reveals transcriptome re-programming of Taxus × media cells to the elicitation with methyl jasmonate
    • Sun, G., Yang, Y., Xie, F., Wen, J.-F., Wu, J., Wilson, I. W., Tang, Q., Liu, H., and Qiu, D. (2013) Deep sequencing reveals transcriptome re-programming of Taxus × media cells to the elicitation with methyl jasmonate PLoS One 8, e62865 10.1371/journal.pone.0062865
    • (2013) PLoS One , vol.8 , pp. e62865
    • Sun, G.1    Yang, Y.2    Xie, F.3    Wen, J.-F.4    Wu, J.5    Wilson, I.W.6    Tang, Q.7    Liu, H.8    Qiu, D.9
  • 21
    • 79959472680 scopus 로고    scopus 로고
    • The first insight into the tissue specific taxus transcriptome via Illumina second generation sequencing
    • Hao, D. C., Ge, G., Xiao, P., Zhang, Y., and Yang, L. (2011) The first insight into the tissue specific taxus transcriptome via Illumina second generation sequencing PLoS One 6, e21220 10.1371/journal.pone.0021220
    • (2011) PLoS One , vol.6 , pp. e21220
    • Hao, D.C.1    Ge, G.2    Xiao, P.3    Zhang, Y.4    Yang, L.5
  • 22
    • 84863091483 scopus 로고    scopus 로고
    • Transcriptional profile of Taxus chinensis cells in response to methyl jasmonate
    • Li, S., Zhang, P., Zhang, M., Fu, C., Zhao, C., Dong, Y., Guo, A., and Yu, L. (2012) Transcriptional profile of Taxus chinensis cells in response to methyl jasmonate BMC Genomics 13, 295 10.1186/1471-2164-13-295
    • (2012) BMC Genomics , vol.13 , pp. 295
    • Li, S.1    Zhang, P.2    Zhang, M.3    Fu, C.4    Zhao, C.5    Dong, Y.6    Guo, A.7    Yu, L.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.