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Toni Kutchan's Laboratory








Click here for Dr. Toni Kutchan's List 

Click here for Dr. Meinhart Zenk's List

Some reprints are available at the links below.  Please note that subscriptions are needed to access some of these reprints.

Toni M. Kutchan Selected representative publications:

Kutchan, T.M., Hampp, N., Lottspeich, F., Beyreuther, K. and Zenk, M.H. The cDNA clone for strictosidine synthase from Rauvolfia serpentina: DNA sequence determination and expression in Escherichia coli. FEBS Lett. 237, 40-44 (1988).
Link to abstract/article

Dittrich, H. and Kutchan, T.M. Molecular cloning, expression and induction of berberine bridge enzyme, an enzyme essential to the formation of benzophenanthridine alkaloids in the response of plants to pathogenic attack. Proc. Natl. Acad. Sci. USA 88, 9969-9973 (1991).
Link to abstract/article

Kraus, P.F.X. and Kutchan, T.M. Molecular cloning and heterologous expression of a cDNA encoding berbamunine synthase, a C-O phenol-coupling cytochrome P-450 from the higher plant Berberis stolonifera. Proc. Natl. Acad. Sci. USA 92, 2071-2075 (1995).
Link to abstract/article

Kutchan, T.M. and Dittrich, H. Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants. J. Biol. Chem. 270, 24475-24481 (1995).
Link to abstract/article

Pauli, H.H. and Kutchan, T.M. Molecular cloning and functional heterologous expression of two alleles encoding (S)-N-methylcoclaurine 3'-hydroxylase (CYP80B1), a new methyl jasmonate-inducible cytochrome P-450 dependent monooxygenase of benzylisoquinoline alkaloid biosynthesis. Plant J. 13, 793-801 (1998).
Link to abstract/article

Unterlinner, B., Lenz, R. and Kutchan, T.M. Molecular cloning and functional expression of codeinone reductase - the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum. Plant J. 18, 465-475 (1999).
Link to abstract/article

Grothe, T., Lenz, R. and Kutchan, T.M. Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum. J. Biol. Chem. 276, 30717-30723 (2001).
Link to abstract/article

Weid, M., Ziegler, J. and Kutchan, T.M. The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy Papaver somniferum. Proc. Natl. Acad. Sci. USA, 101, 13957-13962 (2004).
Link to abstract/article

Ziegler, J., Diaz-Chavez, M.L., Kramell, R., Ammer, C. and Kutchan, T.M. Comparative macroarray analysis of morphine containing Papaver somniferum and eight morphine free Papaver species identifies an O-methyltransferase involved in benzylisoquinoline biosynthesis. Planta 222, 458 - 471 (2005).
Link to abstract/article

Ziegler, J., Voigtlaender, S., Schmidt, J., Kramell, R., Miersch, O., Ammer, C., Gesell, A., and Kutchan, T.M. Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase / reductase involved in morphine biosynthesis. Plant J. 48, 177-192 (2006).
Link to abstract/article

Winkler, A., Kutchan, T.M., Anton Glieder, A., and Macheroux, P. Berberine bridge enzyme possesses a novel bi-covalently attached FAD cofactor linked to a histidine and cysteine residue. J. Biol. Chem. 281, 21276-21285 (2006).
Link to abstract/article

Winkler, A., Kutchan, T.M. and Macheroux, P. 6-S-Cysteinylation of bi-covalently attached FAD in berberine bridge enzyme tunes the redox potential for optimal activity J. Biol. Chem. 282, 24437-24443 (2007).
Link to abstract/article

Springob, K., Samappito, S., Jindaprasert, A., Schmidt, J., Page, J.E., De-Eknamkul, W. and Kutchan, T.M. A polyketide synthase of Plumbago indica that catalyzes the formation of a hexaketide pyrone. FEBS J. 274, 406-417 (2007).
Link to abstract/article

Larkin, P.J., Miller, J., Allen, R.S., Millgate, A.G., Chitty, J.A., Gerlach, W.L., Frick, S., Kutchan, T.M. and Fist, A.J. Increasing morphinan alkaloid production by overexpressing codeinone reductase in transgenic Papaver somniferum. Plant Biotech. J. 5, 26-37 (2007).
Link to abstract/article

Frick, S., Kramell, R. and Kutchan, T.M. Metabolic engineering of a morphine biosynthetic P450 in opium poppy surpasses breeding. Metabolic Engineering 9, 169-176 (2007).
Link to abstract/article

Jindaprasert, A., Springob, K., Schmidt, J., De-Eknamkul, W. and Kutchan, T.M. Pyrone polyketides synthesized by a type III polyketide synthase from Drosophyllum lusitanicum. Phytochemistry  doi:10.1016/j.phytochem.2008.03.013 (2008).
Link to abstract/article

Winkler, A., Lyskowski, A., Riedl, S., Puhl, M., Kutchan, T.M., Macheroux, P. and Gruber, K. A concerted mechanism for berberine bridge enzyme. Nat. Chem. Biol.  doi:10.1038/nchembio.123 (2008).
Link to abstract/article

Nomura, T., Lara Quesada, A., Kutchan, T.M. The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha. J. Biol. Chem.  doi:10.1074/jbc.M806953200 (2008).
Link to abstract/article



Meinhart H. Zenk selected representative publications:

Nagakura, N., Rueffer, M., Zenk, M. H. (1979): "The biosynthesis of monoterpenoid indole alkaloids from strictosidine." Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999): 2308-2312.
Link to abstract/article

Grill, E., Winnacker, E. L., Zenk, M. H. (1985): "Phytochelatins: the principal heavy-metal complexing peptides of higher plants." Science 230: 674-676.
Link to abstract/article

Streber, W. R., Timmis, K. N., Zenk, M. H. (1987): "Analysis, cloning, and high-level expression of 2,4-dichlorophenoxyacetate monooxygenase gene tfdA of Alcaligenes eutrophus JMP134." J. Bacteriol. 169: 2950-2955.
Link to abstract/article

Zenk, M. H., Gerardy, R., Stadler, R. (1989): "Phenol oxidative coupling of benzylisoquinoline alkaloids is catalyzed by region- and stereo-selective cytochrome P450 linked plant enzymes: salutaridine and berbamunine." J. Chem. Soc., Chem. Commun. 22: 1725-1727.
Link to abstract/article

Stadler, R., Zenk, M. H. (1990): "A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline alkaloid reticuline." Liebigs Ann. Chem.: 555-562.
Link to abstract/article

Gundlach, H., Mueller, M. J., Kutchan, T. M., Zenk, M. H. (1992): "Jasmonic acid is a signal transducer in elicitor-induced plant cell cultures." Proceedings of the National Academy of Sciences of the United States of America 89: 2389-2393.
Link to abstract/article

Lotter, H., Gollwitzer, J., Zenk, M. H. (1992): "Revision of the configuration at C-7 of salutaridinol-I, the natural intermediate in morphine biosynthesis." Tetrahedron Lett. 33: 2443-2446.
Link to abstract/article

Lenz, R., Zenk, M. H. (1995): "Acetyl coenzyme A:salutaridinol-7-O-acetyltransferase from Papaver somniferum plant cell cultures. The enzyme catalyzing the formation of thebaine in morphine biosynthesis." J. Biol. Chem. 270: 31091-31096.
Link to abstract/article

Zenk, M. H. (1996): "Heavy metal detoxification in higher plants - a review." Gene 179: 21-30.
Link to abstract/article

Eisenreich, W., Schwarz, M., Cartayrade, A., Arigoni, D., Zenk, M. H., Bacher, A. (1998): "The deoxyxylulose phospate pathway of terpenoid biosynthesis in plants and microorganisms." Chem. Biol. 5: R221-R233.
Link to abstract/article

Raith, K., Neubert, R., Poeaknapo, C., Boettcher, C., Schmidt, J., Zenk, M. H. (2003): "Electrospray tandem mass spectrometric investigations of morphinans." Am. Soc. Mass Spectr. 14: 1262-1269.
Link to abstract/article

Poeaknapo, C., Schmidt, J., Brandsch, M., Draeger, B., Zenk, M. H. (2004): "Endogenous formation of morphine in human cells." Proceedings of the National Academy of Sciences of the United States of America 101: 14091-14096.
Link to abstract/article

Boettcher, C., Fellermeier, M., Boettcher, C., Draeger, B., Zenk, M. H. (2005): "How human neuroblastoma cells make morphine." Proceedings of the National Academy of Sciences of the United States of America 102: 8495-9500.
Link to abstract/article

Nikolaev, V. O., Boettcher, C., Dees, C., Buenemann, M., Lohse, M. J., Zenk, M. H. (2007): "Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors." J. Biol. Chem. 282: 27126-27132.
Link to abstract/article

Schmidt, J., Boettcher, C., Kuhnt, C., Kutchan, T. M., Zenk, M. H. (2007): "Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding." Phytochemistry 68: 189-202.
Link to abstract/article


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