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Volumn 14, Issue 7, 2018, Pages 738-743

A pathogenesis-related 10 protein catalyzes the final step in thebaine biosynthesis article

Author keywords

[No Author keywords available]

Indexed keywords

OPIATE; PATHOGENESIS RELATED 10 PROTEIN; PROTEIN; THEBAINE; UNCLASSIFIED DRUG; SACCHAROMYCES CEREVISIAE PROTEIN;

EID: 85047828711     PISSN: 15524450     EISSN: 15524469     Source Type: Journal    
DOI: 10.1038/s41589-018-0059-7     Document Type: Article
Times cited : (67)

References (38)
  • 1
    • 85012896729 scopus 로고    scopus 로고
    • Accelerating the semisynthesis of alkaloid-based drugs through metabolic engineering
    • Ehrenworth, A. M. &Peralta-Yahya, P. Accelerating the semisynthesis of alkaloid-based drugs through metabolic engineering. Nat. Chem. Biol. 13, 249-258 (2017).
    • (2017) Nat. Chem. Biol. , vol.13 , pp. 249-258
    • Ehrenworth, A.M.1    Peralta-Yahya, P.2
  • 2
    • 84964515157 scopus 로고    scopus 로고
    • New developments in engineering plant metabolic pathways
    • Tatsis, E. C. &O'Connor, S. E. New developments in engineering plant metabolic pathways. Curr. Opin. Biotechnol. 42, 126-132 (2016).
    • (2016) Curr. Opin. Biotechnol. , vol.42 , pp. 126-132
    • Tatsis, E.C.1    O'Connor, S.E.2
  • 4
    • 84937845964 scopus 로고    scopus 로고
    • Plant science Morphinan biosynthesis in opium poppy requires a P450-oxidoreductase fusion protein
    • Winzer, T. et al. Plant science. Morphinan biosynthesis in opium poppy requires a P450-oxidoreductase fusion protein. Science 349, 309-312 (2015).
    • (2015) Science , vol.349 , pp. 309-312
    • Winzer, T.1
  • 5
    • 84939563893 scopus 로고    scopus 로고
    • Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy
    • Farrow, S. C., Hagel, J. M., Beaudoin, G. A. W., Burns, D. C. &Facchini, P. J. Stereochemical inversion of (S)-reticuline by a cytochrome P450 fusion in opium poppy. Nat. Chem. Biol. 11, 728-732 (2015).
    • (2015) Nat. Chem. Biol. , vol.11 , pp. 728-732
    • Farrow, S.C.1    Hagel, J.M.2    Beaudoin, G.A.W.3    Burns, D.C.4    Facchini, P.J.5
  • 6
    • 85048784947 scopus 로고    scopus 로고
    • Final step in sugar-to-morphine conversion deciphered
    • Service, R.F. Final step in sugar-to-morphine conversion deciphered. Science https://doi.org/10.1126/science.aac6897/ (2015).
    • (2015) Science
    • Service, R.F.1
  • 7
    • 85048835809 scopus 로고    scopus 로고
    • Yeast-based opioid production completed
    • Keener, A.B. Yeast-based opioid production completed. The Scientist https://www.the-scientist.com/?articles.view/articleNo/43739/title/Yeast-Based-Opioid-Production-Completed/ (2015).
    • (2015) The Scientist
    • Keener, A.B.1
  • 8
    • 37049060408 scopus 로고
    • Tilden lecture: The biosynthesis of alkaloids
    • Battersby, A. R. Tilden Lecture: The biosynthesis of alkaloids. Proc. Chem. Soc. 0, 189-228 (1963).
    • (1963) Proc. Chem. Soc. , pp. 189-228
    • Battersby, A.R.1
  • 9
    • 0028245117 scopus 로고
    • Closure of the oxide bridge in morphine biosynthesis
    • Lenz, R. &Zenk, M. H. Closure of the oxide bridge in morphine biosynthesis. Tetrahedr. Lett. 35, 3897-3900 (1994).
    • (1994) Tetrahedr. Lett. , vol.35 , pp. 3897-3900
    • Lenz, R.1    Zenk, M.H.2
  • 10
    • 0029559296 scopus 로고
    • Acetyl coenzyme A:Salutaridinol-7-Oacetyltransferase from Papaver somniferum plant cell cultures the enzyme catalyzing the formation of thebaine in morphine biosynthesis
    • Lenz, R. &Zenk, M. H. Acetyl coenzyme A:salutaridinol-7-Oacetyltransferase from Papaver somniferum plant cell cultures. The enzyme catalyzing the formation of thebaine in morphine biosynthesis. J. Biol. Chem. 270, 31091-31096 (1995).
    • (1995) J. Biol. Chem. , vol.270 , pp. 31091-31096
    • Lenz, R.1    Zenk, M.H.2
  • 11
    • 0014035116 scopus 로고
    • Phenol oxidation and biosynthesis Part XII Stereochemical studies related to the biosynthesis of the morphine alkaloids
    • Barton, D. H. R., Bhakuni, D. S., James, R. &Kirby, G. W. Phenol oxidation and biosynthesis. Part XII. Stereochemical studies related to the biosynthesis of the morphine alkaloids. J. Chem. Soc. 0, 128-132 (1967).
    • (1967) J. Chem. Soc. , pp. 128-132
    • Barton, D.H.R.1    Bhakuni, D.S.2    James, R.3    Kirby, G.W.4
  • 12
    • 0026525248 scopus 로고
    • Revision of the configuration at C-7 of salutaridinol-I, the natural intermediate in morphine biosynthesis
    • Lotter, H., Gollwitzer, J. &Zenk, M. H. Revision of the configuration at C-7 of salutaridinol-I, the natural intermediate in morphine biosynthesis. Tetrahedr. Lett. 33, 2443-2446 (1992).
    • (1992) Tetrahedr. Lett. , vol.33 , pp. 2443-2446
    • Lotter, H.1    Gollwitzer, J.2    Zenk, M.H.3
  • 13
    • 84878001183 scopus 로고    scopus 로고
    • Benzylisoquinoline alkaloid metabolism: A century of discovery and a brave new world
    • Hagel, J. M. &Facchini, P. J. Benzylisoquinoline alkaloid metabolism: a century of discovery and a brave new world. Plant Cell Physiol. 54, 647-672 (2013).
    • (2013) Plant Cell Physiol. , vol.54 , pp. 647-672
    • Hagel, J.M.1    Facchini, P.J.2
  • 14
    • 44949127129 scopus 로고    scopus 로고
    • Alkaloid biosynthesis: Metabolism and trafficking
    • Ziegler, J. &Facchini, P. J. Alkaloid biosynthesis: metabolism and trafficking. Annu. Rev. Plant Biol. 59, 735-769 (2008).
    • (2008) Annu. Rev. Plant Biol. , vol.59 , pp. 735-769
    • Ziegler, J.1    Facchini, P.J.2
  • 15
    • 42249094600 scopus 로고    scopus 로고
    • Thebaine synthase: A new enzyme in the morphine pathway in Papaver somniferum
    • Fisinger, U., Grobe, N. &Zenk, M. H. Thebaine synthase: a new enzyme in the morphine pathway in Papaver somniferum. Nat. Prod. Commun. 2, 249-253 (2007).
    • (2007) Nat. Prod. Commun. , vol.2 , pp. 249-253
    • Fisinger, U.1    Grobe, N.2    Zenk, M.H.3
  • 16
    • 13344267827 scopus 로고
    • Investigations on the biosynthesis of morphine alkaloids
    • Barton, D. H. R. et al. Investigations on the biosynthesis of morphine alkaloids. J. Chem. Soc. 65, 2423-2438 (1965).
    • (1965) J. Chem. Soc. , vol.65 , pp. 2423-2438
    • Barton, D.H.R.1
  • 17
    • 0142257918 scopus 로고    scopus 로고
    • Electrospray tandem mass spectrometric investigations of morphinans
    • Raith, K. et al. Electrospray tandem mass spectrometric investigations of morphinans. J. Am. Soc. Mass Spectrom. 14, 1262-1269 (2003).
    • (2003) J. Am. Soc. Mass Spectrom. , vol.14 , pp. 1262-1269
    • Raith, K.1
  • 18
    • 0034909349 scopus 로고    scopus 로고
    • Identification of ozone-oxidation products of oxycodone by electrospray ion trap mass spectrometry
    • Pennanen, K., Kotiaho, T., Huikko, K. &Kostiainen, R. Identification of ozone-oxidation products of oxycodone by electrospray ion trap mass spectrometry. J. Mass Spectrom. 36, 791-797 (2001).
    • (2001) J. Mass Spectrom. , vol.36 , pp. 791-797
    • Pennanen, K.1    Kotiaho, T.2    Huikko, K.3    Kostiainen, R.4
  • 20
    • 84874494513 scopus 로고    scopus 로고
    • Structural and functional aspects of PR-10 proteins
    • Fernandes, H., Michalska, K., Sikorski, M. &Jaskolski, M. Structural and functional aspects of PR-10 proteins. FEBS J. 280, 1169-1199 (2013).
    • (2013) FEBS J. , vol.280 , pp. 1169-1199
    • Fernandes, H.1    Michalska, K.2    Sikorski, M.3    Jaskolski, M.4
  • 21
    • 78649499936 scopus 로고    scopus 로고
    • Norcoclaurine synthase is a member of the pathogenesis-related 10/Bet v1 protein family
    • Lee, E.-J. &Facchini, P. Norcoclaurine synthase is a member of the pathogenesis-related 10/Bet v1 protein family. Plant Cell 22, 3489-3503 (2010).
    • (2010) Plant Cell , vol.22 , pp. 3489-3503
    • Lee, E.-J.1    Facchini, P.2
  • 22
    • 84857995434 scopus 로고    scopus 로고
    • Microbial production of indolylglucosinolate through engineering of a multi-gene pathway in a versatile yeast expression platform
    • Mikkelsen, M. D. et al. Microbial production of indolylglucosinolate through engineering of a multi-gene pathway in a versatile yeast expression platform. Metab. Eng. 14, 104-111 (2012).
    • (2012) Metab. Eng. , vol.14 , pp. 104-111
    • Mikkelsen, M.D.1
  • 23
    • 84860840868 scopus 로고    scopus 로고
    • Integration of deep transcript and targeted metabolite profiles for eight cultivars of opium poppy
    • Desgagné-Penix, I., Farrow, S. C., Cram, D., Nowak, J. &Facchini, P. J. Integration of deep transcript and targeted metabolite profiles for eight cultivars of opium poppy. Plant Mol. Biol. 79, 295-313 (2012).
    • (2012) Plant Mol. Biol. , vol.79 , pp. 295-313
    • Desgagné-Penix, I.1    Farrow, S.C.2    Cram, D.3    Nowak, J.4    Facchini, P.J.5
  • 24
    • 84866500452 scopus 로고    scopus 로고
    • Biochemical genomics for gene discovery in benzylisoquinoline alkaloid biosynthesis in opium poppy and related species
    • Dang, T. T., Onoyovwi, A., Farrow, S. C. &Facchini, P. J. Biochemical genomics for gene discovery in benzylisoquinoline alkaloid biosynthesis in opium poppy and related species. Methods Enzymol. 515, 231-266 (2012).
    • (2012) Methods Enzymol. , vol.515 , pp. 231-266
    • Dang, T.T.1    Onoyovwi, A.2    Farrow, S.C.3    Facchini, P.J.4
  • 26
    • 84887586519 scopus 로고    scopus 로고
    • Gene clustering in plant specialized metabolism
    • Nützmann, H.-W. &Osbourn, A. Gene clustering in plant specialized metabolism. Curr. Opin. Biotechnol. 26, 91-99 (2014).
    • (2014) Curr. Opin. Biotechnol. , vol.26 , pp. 91-99
    • Nützmann, H.-W.1    Osbourn, A.2
  • 27
    • 84862983375 scopus 로고    scopus 로고
    • A Papaver somniferum 10-gene cluster for synthesis of the anticancer alkaloid noscapine
    • Winzer, T. et al. A Papaver somniferum 10-gene cluster for synthesis of the anticancer alkaloid noscapine. Science 336, 1704-1708 (2012).
    • (2012) Science , vol.336 , pp. 1704-1708
    • Winzer, T.1
  • 28
    • 59449099013 scopus 로고    scopus 로고
    • Structural basis of enzymatic (S)-norcoclaurine biosynthesis
    • Ilari, A. et al. Structural basis of enzymatic (S)-norcoclaurine biosynthesis. J. Biol. Chem. 284, 897-904 (2009).
    • (2009) J. Biol. Chem. , vol.284 , pp. 897-904
    • Ilari, A.1
  • 29
    • 85027917295 scopus 로고    scopus 로고
    • Crystal structure of norcoclaurine-6-O-methyltransferase, a key rate-limiting step in the synthesis of benzylisoquinoline alkaloids
    • Robin, A. Y., Giustini, C., Graindorge, M., Matringe, M. &Dumas, R. Crystal structure of norcoclaurine-6-O-methyltransferase, a key rate-limiting step in the synthesis of benzylisoquinoline alkaloids. Plant J. 87, 641-653 (2016).
    • (2016) Plant J. , vol.87 , pp. 641-653
    • Robin, A.Y.1    Giustini, C.2    Graindorge, M.3    Matringe, M.4    Dumas, R.5
  • 30
    • 77956032037 scopus 로고    scopus 로고
    • Biomimetic synthesis of (-)-pycnanthuquinone C through the Diels-Alder reaction of a vinyl quinone
    • Löbermann, F., Mayer, P. &Trauner, D. Biomimetic synthesis of (-)-pycnanthuquinone C through the Diels-Alder reaction of a vinyl quinone. Angew. Chem. Int. Ed. Engl. 49, 6199-6202 (2010).
    • (2010) Angew. Chem. Int. Ed. Engl. , vol.49 , pp. 6199-6202
    • Löbermann, F.1    Mayer, P.2    Trauner, D.3
  • 31
  • 32
    • 0001021840 scopus 로고
    • Identification and characterization of latex-specific proteins in opium poppy
    • Nessler, C. L., Allen, R. D. &Galewsky, S. Identification and characterization of latex-specific proteins in opium poppy. Plant Physiol. 79, 499-504 (1985).
    • (1985) Plant Physiol. , vol.79 , pp. 499-504
    • Nessler, C.L.1    Allen, R.D.2    Galewsky, S.3
  • 33
    • 67349278136 scopus 로고    scopus 로고
    • Automated unrestricted multigene recombineering for multiprotein complex production
    • Bieniossek, C. et al. Automated unrestricted multigene recombineering for multiprotein complex production. Nat. Methods 6, 447-450 (2009).
    • (2009) Nat. Methods , vol.6 , pp. 447-450
    • Bieniossek, C.1
  • 34
    • 84859159395 scopus 로고    scopus 로고
    • Transcript and metabolite profiling in cell cultures of 18 plant species that produce benzylisoquinoline alkaloids
    • Farrow, S. C., Hagel, J. M. &Facchini, P. J. Transcript and metabolite profiling in cell cultures of 18 plant species that produce benzylisoquinoline alkaloids. Phytochemistry 77, 79-88 (2012).
    • (2012) Phytochemistry , vol.77 , pp. 79-88
    • Farrow, S.C.1    Hagel, J.M.2    Facchini, P.J.3
  • 35
    • 84942894278 scopus 로고    scopus 로고
    • Isolation and characterization of O-methyltransferases involved in the biosynthesis of glaucine in Glaucium flavum
    • Chang, L., Hagel, J. M. &Facchini, P. J. Isolation and characterization of O-methyltransferases involved in the biosynthesis of glaucine in Glaucium flavum. Plant Physiol. 169, 1127-1140 (2015).
    • (2015) Plant Physiol. , vol.169 , pp. 1127-1140
    • Chang, L.1    Hagel, J.M.2    Facchini, P.J.3
  • 36
    • 84964258842 scopus 로고    scopus 로고
    • Plug-and-play benzylisoquinoline alkaloid biosynthetic gene discovery in engineered yeast
    • Morris, J. S. et al. Plug-and-play benzylisoquinoline alkaloid biosynthetic gene discovery in engineered yeast. Methods Enzymol. 575, 143-178 (2016).
    • (2016) Methods Enzymol. , vol.575 , pp. 143-178
    • Morris, J.S.1
  • 37
    • 33845883022 scopus 로고    scopus 로고
    • Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding
    • Schmidt, J., Boettcher, C., Kuhnt, C., Kutchan, T. M. &Zenk, M. H. Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding. Phytochemistry 68, 189-202 (2007).
    • (2007) Phytochemistry , vol.68 , pp. 189-202
    • Schmidt, J.1    Boettcher, C.2    Kuhnt, C.3    Kutchan, T.M.4    Zenk, M.H.5
  • 38
    • 57849148656 scopus 로고    scopus 로고
    • A rapid and effective method for RNA extraction from different tissues of grapevine and other woody plants
    • Gambino, G., Perrone, I. &Gribaudo, I. A rapid and effective method for RNA extraction from different tissues of grapevine and other woody plants. Phytochem. Anal. 19, 520-525 (2008).
    • (2008) Phytochem. Anal. , vol.19 , pp. 520-525
    • Gambino, G.1    Perrone, I.2    Gribaudo, I.3


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