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Single-cell multi-omics enabled discovery of alkaloid biosynthetic pathway genes in the medical plant Catharanthus roseus.

Li, C., Wood, J.C., Vu, A.H., Hamilton, J.P., Lopez, C.E.R., Payne, R.M.E., Serna Guerrero, D.A., Yamamoto, K., Vaillancourt, B., Caputi, L.*, O’Connor, S.E.*, Buell, C.R.*

Bioarchive

doi: https://doi.org/10.1101/2022.07.04.498697

Recycling Upstream Redox Enzymes Expands the Regioselectivity of Cycloaddition in Pseudo-Aspidosperma Alkaloid Biosynthesis.

Kamileen, M.O., DeMars, M.D. 2nd, Hong, B., Nakamura, Y., Paetz, C., Lichman, B.R., Sonawane, P.D., Caputi, L.*, O'Connor, S.E.* (2022)

J. Am. Chem. Soc. 144, 19673-19679.

Expansion of the catalytic repertoire of alcohol dehydrogenases in plant metabolism.

Langley, C., Tatsis, E., Hong, B., Nakamura, Y., Paetz, C., Stevenson, C.E.M., Basquin, J., Lawson, D.M., Caputi, L.*, O’Connor, S.E.* (2022) Angew. Chem. Intl. Ed. 61, e202210934

Reconstitution of monoterpene indole alkaloid biosynthesis in Nicotiana benthamiana.

Dudley, Q.M., Jo, S., Serna Guerrero, D.A., O’Connor, S.E., Caputi, L.*, Patron, N.J.* (2022)

Communications Biology, 5, 949.

Biosynthesis of iridoid sex pheromones in aphids.

Koellner, T.G.*, David, A., Luck, K., Kunert, G., Beran, F., Zhou, J.-J., Caputi, L., O’Connor, S.E.* (2022) Proc. Natl. Acad. Sci. 119, e2211254119.

A biocatalytic toolkit for the control of iridoid stereochemistry.

Hernández Lozada, N.J., Hong, B., Wood, J.C., Caputi, L. Basquin, J., Chuang, L., Kunert, M., Rodríguez López, C.E., Langley, C., Zhao, D., Buell, C.R., Lichman, B.R., O'Connor, S.E.* (2022) Nature Commun. 13, 4718.

Biosynthesis of strychnine.

Hong, B., Grzech, D., Caputi, L., Sonawane, P., López, C.E.R., Kamileen, M.O., Hernández Lozada, N.J., Grabe, V., O'Connor, S.E.* (2022) Nature. 207, 617-622.

Directed biosynthesis of new to nature alkaloids in a heterologous Nicotiana benthamiana expression host.

Boccia, M., Grzech, D., Lopes, A.A., O'Connor, S.E.*, Caputi, L.* (2022) Front. Plant Sci. 13, 919443.

A microbial supply chain for production of the anti-cancer drug vinblastine.

Zhang, J., Hansen, L.G., Gudich, O., Viehrig, K., Lassen, L.M.M., Schrübbers, L., Adhikari, K.B., Rubaszka, P, Carrasquer-Alvarez, E., Chen, L., D'Ambrosio, V., Lehka, B., Haidar, A.K., Nallapareddy, S., Giannakou, K., Laloux, M., Arsovska, D., Jørgensen, M.A.K., Chan, L.J.G., Kristensen, M., Christensen, H.B., Sudarsan, S., Stander, E.A., Baidoo, E., Petzold, C.J., Wulff, T., O'Connor, S.E., Courdavault, V., Jensen, M.K.*, Keasling, J.D.* (2022) Nature. 609, 341-347.

Imaging MS Analysis in Catharanthus roseus.

Yamamoto, K., Takahashi, K., O'Connor, S.E., Mimura, T.* (2022) Methods Mol. Biol. 2505, 33-43.

More than a Catharanthus plant: A multicellular and pluri-organelle alkaloid-producing factory.

Kulagina, N., Méteignier, L.V., Papon, N., O'Connor, S.E., Courdavault, V.* (2022) Curr. Opin. Plant Biol. 2022, 67, 102200.

Phylogeny-aware chemoinformatic analysis of chemical diversity in the Lamiaceae enables iridoid pathway assembly and discovery of aucubin synthase.

Rodríguez-López, C.E.*, Jiang, Y., Kamileen, M.O., Lichman, B.R., Hong, B., Vaillancourt, B., Buell, C.R., O'Connor, S.E.* (2022) Mol. Biol. Evol. 39, msac057.

Peroxisome Targeting of γ-tocopherol N-methyltransferase Homologs Involved in the Synthesis of Monoterpene Indole Alkaloids.

Koudounas, K., Guirimand, G., Rojas Hoyos, L.F., Carqueijeiro, I., Lemos Cruz, P., Stander, E., Kulagina, N., Perrin, J, Oudin, A., Besseau, S., Lanoue, A., Atehortùa, L., St-Pierre, B., Giglioli-Guivarc'h, N., Papon, N., O'Connor, S.E., Courdavault, V. (2022) Plant Cell Physiol. 63, 200-216.

Genome assembly of the medicinal plant Voacanga thouarsii.

Cuello, C., Stander, E.A., Jansen, H.J., Dugé de Bernonville, T., Lanoue, A., Giglioli-Guivarc'h, N., Papon, N., Dirks, R.P., Jensen, M.K., O'Connor, S.E., Besseau, S., Courdavault, V.* (2022) Genome Biol. Evol. 14, evac158.

In vivo characterization of key iridoid biosynthesis pathway genes in catnip (Nepeta cataria).

Palmer, L., Chuang, L., Siegmund, M., Kunert, M., Yamamoto, K., Sonawane, P.D., O’Connor, S.E.* (2022) Planta, 256, 99.

The Vinca minor genome highlights conserved evolutionary traits in monoterpene indole alkaloid synthesis.

Stander, E.A., Cuello C., Birer-Williams, C., Kulagina, N., Jansen, H., Carqueijeiro, I., Méteignier, L.V., Vergès, V., Oudin A., Papon, N., Dirks, R., Jensen, M.K., O'Connor, S.E., Dugé de Bernonville, T., Besseau, S., Courdavault, V.* (2022) . G3, jkac268.

Improved virus-induced gene silencing allows discovery of a serpentine synthase gene in Catharanthus roseus.

Yamamoto, K., Grzech, D., Koudounas, K., Stander, E.A., Caputi, L., Mimura, T., Courdavault, V., O'Connor, S.E. (2021) Plant Physiol. 187, 846-857.

Cell-free total biosynthesis of plant terpene natural products using an orthogonal cofactor regeneration system.

Bat-Erdene, U., Billingsley, J.M., Turner, W.C., Lichman, B.R., Ippoliti, F.M., Garg, N.K., O'Connor, S.E., Tang, Y.* (2021) ACS Catal. 11, 9898-9903.

Metabolic engineering for plant natural products biosynthesis: new procedures, concrete achievements and remaining limits.

Courdavault, V., O'Connor, S.E., Jensen, M.K., Papon, N. (2021) Nat Prod Rep. 38, 2145-2153.

Early and late steps of quinine biosynthesis.

Trenti, F., Yamamoto, K., Hong, B., Paetz, C., Nakamura, Y., O'Connor, S.E.* (2021) Org Lett. 23, 1793-1797.

The Mitragyna speciosa (Kratom) genome: a resource for data-mining potent pharmaceuticals that impact human health.

Brose, J., Lau, K.H., Dang, T.T.T., Hamilton, J.P., Martins, L.D.V., Hamberger, B., Hamberger, B., Jiang, J., O'Connor, S.E., Buell, C.R.* (2021) G3, 11, jkab058.

Symbionts, peptides, and (no) iron: How ants defend their fungal crop.

O'Connor, S.E. (2021) ACS Cent. Sci. 7, 225-227.

Two bi-functional cytochrome P450 CYP72 enzymes from olive (Olea europaea) catalyze the oxidative C-C bond cleavage in the biosynthesis of secoxy-iridoids - flavor and quality determinants in olive oil.

Rodríguez-López, C.E., Hong, B., Paetz, C., Nakamura, Y., Koudounas, K., Passeri, V., Baldoni, L., Alagna, F., Calderini, O., O'Connor, S.E.* (2021) New Phytol. 229, 2288-2301.

Alternative splicing directs a pseudo-strictosidine β-D-glucosidase modulating alkaloid synthesis.

Carqueijeiro, I., Koudounas, K., Dugé de Bernonville, T., Sepúlveda, L.J., Mosquera, A., Bomzan, P.D., Oudin, A., Lanoue, A., Besseau, S., Cruz, P.L., Kulagina, N., Stander, E.A., Burlaud-Gaillard, J., Blanchard, E., Clastre, M., Atehortùa, L., St-Pierre, B., Giglioli-Guivarc’h, N., Papon, N., Nagegowda, D.A., O’Connor, S.E., Courdavault, V. (2020) Plant Physiol. 185, 836-856.

Nicotiana benthamiana as a transient expression host to produce auxin analogs.

Davis, K., Gkotsi, D.S., Smith, D.R.M., Goss, R.J.M., Caputi, L., O'Connor, S.E.* (2020) Front Plant Sci. 11, 581675.

Identifying Genes Involved in alkaloid Biosynthesis in Vinca minor through transcriptomics and gene co-expression analysis.

Stander, E.A., Sepúlveda, L.J., Dugé de Bernonville, T., Carqueijeiro, I., Koudounas, K., Cruz, P.L., Besseau, S., Lanoue, A., Papon, N., NGiglioli-Guivarc’h, N., Dirks, R., O’Connor, S.E., Atehortùa, L., Oudin, A., Courdavault, V. (2020) Biomolecules. 10, 1595.

The Progesterone 5β-Reductase/Iridoid Synthase Family: A Catalytic Reservoir for Specialized Metabolism across Land Plants.

Nguyen, T.D., O'Connor, S.E.* (2020) ACS Chem Biol. 15, 1780-1787.

SI here

The evolutionary origins of the cat attractant nepetalactone in catnip.

Lichman, B.R.*, Godden, G.T., Hamilton, J.P., Palmer ,L., Kamileen, M.O., Zhao, D., Vaillancourt, B., Wood, J.C., Sun, M., Kinser, T.J., Henry, L.K., Rodriguez-Lopez, C., Dudareva, N., Soltis, D.E., Soltis, P.S., Buell, C.R.*, O'Connor, S.E.* (2020) Sci Adv. 6, eaba0721.

SI here

Towards the microbial production of plant-derived anticancer drugs.

Courdavault, V., O’Connor, S.E., Oudin, A., Besseau, S., Papon, N. (2020)

Trends Cancer 6, 444-448

Hairy root transformation of Brassica rapa with bacterial halogenase genes and regeneration to adult plants to modify production of indolic compounds.

Neumann, M., Prahl, S., Caputi, L., Hill, L., Kular, B., Walter, A., Patallo, E.P., Milbredt, D., Aires, A., Schöpe, M., O'Connor, S., van Pée, K.H., Ludwig-Müller, J. (2020) Phytochemistry. 175, 112371.

Chlorinated auxins-How does Arabidopsis thaliana deal with them?

Walter, A., Caputi, L., O'Connor, S., van Pée, K.H., Ludwig-Müller, J. (2020) Int J Mol Sci. 21, 2567.

Virus-induced gene silencing: Hush genes to make them talk

Courdavault, C., Besseau, S., Oudin, A., Papon, N., O’Connor, S.E. (2020) Trends Plant Sci. 25, 714-715.

Identifying missing biosynthesis enzymes of plant natural products.

de Bernonville, T. D., Papon, N., Clastre, M., O’Connor, S. E., Courdavaul, V. (2020)

Trends Pharm. Sci. 41, 142-146.

Structural basis of cycloaddition in biosynthesis of iboga and aspidosperma alkaloids.

Caputi, L.#, Franke, J. #, Bussey, K., Farrow, S. C., Curcino Vieira, I. J., Stevenson, C. E. M., Lawson, D. M., O'Connor, S. E.* (2020) Nat. Chem. Biol. 16, 383-386.

Supporting Information.

for a pdf also click this link:

https://rdcu.be/b1Oeb

Developmental methylome of the medicinal plant Catharanthus roseus unravels the tissue-specific control of the monoterpene indole alkaloid pathway by DNA methylation.

Dugé de Bernonville, T., Maury, S., Delaunay, A., Daviaud, C., Chaparro, C., Tost, J., O'Connor, S.E., Courdavault V. (2020) Int. J. Mol. Sci. 21, E6028.

Biosynthesis of vinblastine.

Chung, K., O’Connor, S.E. (2020) In: Hung-Wen (Ben) Liu, Tadhg P. Begley (eds.) Comprehensive Natural Products III: Chemistry and Biology. vol. 2, pp. 642-

685.

Metabolomics analysis reveals tissue-specific metabolite compositions in leaf blade and traps of carnivorous Nepenthes plants.

Dávila-Lara, A., Rodríguez-López, C.E., O'Connor, S.E., Mithöfer, A. (2020) Int. J. Mol. Sci. 21, 4376.

Synthesis of (−)-Melodinine K: A case study of efficiency in natural product synthesis.
Walia, M., Teijaro, C.N., Gardner, A., Tran, T., Kang, J., Zhao, S., O'Connor, S.E., Courdavault, V., Andrade, R.B. (2020) . J. Nat. Prod. 83, 2425-2433.

Beyond the semi-synthetic artemisinin: metabolic engineering of plant-derived anti-cancer drugs.

Carqueijeiro, I., Langley, C., Grzech, D., Koudouna,s K., Papon, N., O'Connor, S. E., Courdavault V. (2019) Curr. Opin. Biotechnol. 65, 17-24.

The complexity of intercellular localisation of alkaloids revealed by single-cell metabolomics.

Yamamoto, K., Takahashi, K., Caputi, L., Mizuno, H., Rodriguez-Lopez, C. E., Iwasaki, T., Ishizaki, K., Fukaki, H., Ohnishi, M., Yamazaki, M., Masujima, T., O'Connor, S. E., Mimura, T.* (2019) New Phytol. 224, 848-859.

Biosynthesis of an anti-addiction agent from the Iboga plant.

Farrow, S. C., Kamileen, M. O., Caputi, L., Bussey, K., Mundy, J. E. A., McAtee, R. C., Stephenson, C. R. J., O'Connor, S. E.* (2019) J. Am. Chem. Soc. 141, 12979-12983.

Biocatalytic strategies towards [4+2] cycloadditions.

Lichman, B. R., O'Connor, S. E., Kries, H. (2019) Chemistry. 25, 6864-6877.

A database-driven approach identifies additional diterpene synthase activities in the mint family (Lamiaceae).

Johnson, S. R., Bhat, W. W., Bibik, J., Turmo, A., Hamberger, B. (2019) Evolutionary Mint Genomics Consortium, Hamberger B. (2019) J. Biol. Chem. 294, 1349-1362.

Uncoupled activation and cyclisation in catmint reductive terpenoid biosynthesis.

Lichman, B. R., Kamileen, M. O., Titchiner, G. R., Saalbach, G., Stevenson, C. E. M., Lawson, D. M., O’Connor, S. E.* (2019) Nat. Chem. Biol. 15, 71-79

Conserved gene clusters in monoterpene indole alkaloid biosynthesis enable gene discovery in Gelsemium sempervirens.

Franke, J., Kim, J., Hamilton, J. P., Zhao, D., Pham, G. M., Wiegert-Rininger, K., Crisovan, E., Newton, L., Vaillancourt, B., Tatsis, E. C., Buell, C. R.*, O’Connor, S. E.* (2018) ChemBioChem

Cytochrome P450 and O-methyltransferase catalyze the final steps in the biosynthesis of the anti-addictive alkaloid ibogaine from Tabernanthe iboga.

Farrow, S. C., Kamileen, M. O., Meades, J., Ameyaw, B., Xiao, Y., O'Connor, S. E.* (2018) J. Biol. Chem. 293, 13821-13833.

Two tabersonine 6,7-epoxidases start synthesis of lochnericine-type alkaloids in Catharanthus roseus.

Carqueijeiro, I., Brown, S., Chung, K., Dang, T. T. T., Dugé de Bernonville, T., Lanoue, A., Dang, T. T., Teijaro, C., Paetz, C., Billet, K., Mosquera, A., Oudin, A., Besseau, S., Papon, N., Glévarec, G., Atehortùa, L., Clastre, M., Giglioli-Guivarc’h, N., St Pierre, B., Andrade, R., O'Connor, S., Courdavault, V. (2018) Plant Physiol. 177, 1473-1486.

Vacuole-Targeted Proteins: Ins and Outs of Subcellular Localization Studies.

Carqueijeiro, I., Sepúlveda, L. J., Mosquera, A., Payne, R., Corbin, C., Papon, N., de Bernonville, T. D., Besseau, S., Lanoue, A., Glévarec, G., Clastre, M., St-Pierre, B., Atehortùa, L., Giglioli-Guivarc'h, N., O'Connor, S. E., Oudin, A., Courdavault, V. (2018) Methods Mol. Biol. 1789, 33-54.

Phylogenomic mining of the mints: elucidating evolution in a chemically diverse clade.

The Mint Consortium. (2018) Mol. Plant. 11, 1084-1096.

Cyclization vs. aromatization: The substrate-guided double face of cytochrome P450 homologues provides entry into both sarpagan and β-carboline alkaloids.

Dang, T. T. T., Franke, J., Carqueijeiro, I., Langley, C., Courdavault, V., O’Connor, S. E.* (2018) Nat. Chem. Biol. 14, 760-763.

Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle.

Caputi, L., Franke, J., Farrow, S. C., Chung, K., Payne, R. M. E., Nguyen, T.-D.,Dang, T. T. T., Carqueijeiro, I. S. T., Koudounas, K., Dugé de Bernonville, T., Ameyaw, B., Jones, D. M., Vieira, I. J. C., Courdavault, V.*, O'Connor, S. E.* (2018) Science. 360, 1235-1239.

Pressure Test to Make 10 Molecules in 90 Days: External Evaluation of Methods to Engineer Biology.

Casini, A., Chang, F.-Y., Eluere, R., King, A., Young, E., Dudley, Q., Karim, A., Pratt, K., Bristol, C., Forget, A., Ghodasara, A., Warden-Rothman, R., Gan, R., Cristofaro, A., Espah Borujeni, A., Ryu, M.-H., Li, J., Kwon, Y., Wang, H., Tatsis, E., Rodriguez-Lopez, C., O'Connor, S., Medema, M., Fischbach, M., Jewett, M., Voigt, C., Gordon, D. B. (2018) A J. Am. Chem. Soc. 140, 4302-4316.

A novel BAHD acyltransferase catalyzing 19-O-acetylation of tabersonine derivatives in roots of Catharanthus roseus enables combinatorial synthesis of new-to-nature monoterpene indole alkaloids.

Carqueijeiro, I., Dugé de Bernonville, T., Lanoue, A., Dang, T. T., Teijaro, C., Paetz, C., Billet, K., Mosquera, A., Oudin, A., Besseau, S., Papon, N., Glévarec, G., Atehortùa, L., Clastre, M., Giglioli-Guivarc’h, N., Schneider, B., St Pierre, B., Andrade, R., O'Connor, S., Courdavault, V. (2018) Plant J. 94, 469-484

Discovery of a short chain dehydrogenase from Catharanthus roseus that produces a novel monoterpene indole alkaloid.

Stavrinides, A. K., Tatsis, E. C., Dang, T. T., Caputi, L., Stevenson, C. E. M., Lawson, D. M., Schneider, B., O’Connor, S. E.* (2018) ChemBioChem. 19, 940-948.

Identification of Iridoid Synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry.

Sherden, N.S., Lichman, B., Caputi, L., Zhao, D., Kamileen, M.O.,Buell, C.R., O'Connor, S.E.* (2018) Phytochemistry 145, 48-56.

Strategies to Produce Chlorinated Indole-3-Acetic Acid and Indole-3-Acetic Acid Intermediates.

Patallo, E. P., Walter, A., Milbredt, D., Thomas, M., Neumann, M., Caputi, L., O'Connor, S., Ludwig-Müller, J., van Pée, K.-H. (2017) ChemistrySelect. 2, 11148-11153.

A three enzyme system to generate the Strychnos alkaloid scaffold from a central biosynthetic intermediate.

Tatsis, E.C.#, Carqueijeiro, M.I.S.T.#,de Bernonville, T.D., Franke, J., Dang, T.T.T., Oudin, A., Lanoue, A., Lafontaine, F., Stavrinides, A.K., Clastre, M., Courdavault, V.*, O’Connor, S.E.* (2017) Nat. Commun. 8, 316.

Identification of iridoid glucoside transporters in Catharanthus roseus.

Larsen, B., Fuller, V., Pollier, J., Van Moerkercke, A., Schweizer, F., Payne, R., Colinas, M., O’Connor, S.E., Goossens, A., Halkier, B.* (2017) Plant Cell Physiol. 58, 1507-1518.

Inverted stereocontrol of iridoid synthase in snapdragon.

Kries, H., Kellner, F., Kamileen, M.O., O’Connor, S.E.* (2017) J. Biol. Chem. 292, 14659-14667.

Dual catalytic activity of a cytochrome P450 controls bifurcation at a metabolic branch point of alkaloid biosynthesis in Rauwolfia serpentina.

Dang, T.T., Franke, J., Tatsis, E., O'Connor, S.E.* (2017) Angew. Chem. Int. Ed. doi: 10.1002/anie.201705010.

Differential iridoid production as revealed by a diversity panel of 84 cultivated and wild blueberry species.

Leisner, C.P., Kamileen, M.O., Conway, M.E., O'Connor, S.E., Buell, C.R. (2017) PLoS One. 12, e0179417.

Folivory elicits a strong defense reaction in Catharanthus roseus: metabolomic and transcriptomic analyses reveal distinct local and systemic responses.

Dugé de Bernonville, T., Carqueijeiro, I., Lanoue, A., Lafontaine, F., Sánchez Bel, .P, Liesecke, F., Musset, K., Oudin, A., Glévarec, G., Pichon, O., Besseau, S., Clastre, M., St-Pierre, B., Flors, V., Maury, S., Huguet, E., O'Connor, S.E., Courdavault, V. (2017) Sci. Rep. 7, 40453.

An NPF transporter exports a central monoterpene indole alkaloid intermediate from the vacuole.

Payne, R.M.E., Xu, D., Foureau, E., Soares Teto Carqueijeiro, M. I., Oudin, A., Dugé de Bernonville, T., Novak, V., Burow, M., Olsen, C.-E., Jones, D.M., Tatsis, E.C., Pendle, A., Halkier, B.A., Geu-Flores, F., Courdavault, V., Nour-Eldin, H.H., O’Connor, S. E.* (2017) Nature Plants. 3, 16208.

New developments in engineering plant metabolic pathways.

Tatsis, E.C., O'Connor, S.E. (2016) Curr. Opin. Biotech. 42, 126-132.

Structural characterization of EasH (Aspergillus japonicus) - an oxidase involved in cycloclavine biosynthesis.

Jakubczyk, D., Caputi, L., Stevenson, C.E., Lawson, D.M., O'Connor, S.E.* (2016) Chem. Commun. 52, 14306-14309.

Class II cytochrome P450 reductase governs the biosynthesis of alkaloids.

Parage, C., Foureau, E., Kellner, F., Burlat, V., Mahroug, S., Lanoue, A., Dugé de Bernonville, T., Londono, M.A., Carqueijeiro, I., Oudin, A., Besseau, S., Papon, N., Glévarec, G., Atehortùa, L., Giglioli-Guivarc'h, N., St-Pierre, B., Clastre, M., O'Connor, S.E., Courdavault, V. (2016) Plant Physiol. 172, 1563-1577.

Structural investigation of heteroyohimbine alkaloid synthesis reveals active site elements that control stereoselectivity.

Stavrinides, A., Tatsis, E. C., Caputi, L., Foureau, E., Stevenson, C.E.M., Lawson, D.M., Courdavault, V., O'Connor, S. E.* (2016) Nat. Commun. 12116.

Structural determinants of reductive terpene cyclization in iridoid biosynthesis.

Kries, H., Caputi, L., Stevenson, C.E., Kamileen, M.O., Sherden, N.H., Geu-Flores, F., Lawson, D.M.*, O'Connor, S.E.* (2016) Nat. Chem. Biol. 12, 6-8.

Biocatalysts from alkaloid producing plants.

Kries, H., O’Connor, S.E. (2016) Curr. Opin. Chem. Biol. 31, 22-30.

Ergot alkaloids.

Jakubczyk, D., O'Connor, S. (2016) RSC Drug Discovery Series 50(Privileged Scaffolds in Medicinal Chemistry), 379-397.

Identification and characterization of the iridoid synthase involved in oleuropein biosynthesis in Olive (Olea europaea) fruits.

Alagna, F., Geu-Flores, F., Kries, H., Panara, F., Baldoni, L., O'Connor, S.E., Osbourn, A. (2015) J. Biol. Chem. 29, 5542-5545.

Halogenase engineering for the generation of novel natural products.

Brown S, O'Connor S.* (2015) Chembiochem 6, 2129-2135.

Metabolic engineering of secondary metabolism.

O’Connor, S. E. (2015) Ann. Rev. Gen. 49, 71-94.

Characterization of a second secologanin synthase isoform producing both secologanin and secoxyloganin allows enhanced de novo assembly of a Catharanthus roseus transcriptome.

Dugé de Bernonville, T., Foureau, E., Parage, C., Lanoue, A., Clastre, M., Londono, M.A., Oudin, A., Houillé, B., Papon, N., Besseau, S., Glévarec, G., Atehortùa, L., Giglioli-Guivarc'h, N., St-Pierre, B., De Luca, V., O'Connor, S.E., Courdavault, V. (2015) BMC Genomics 16, 619.

Standards for plant synthetic biology: a common syntax for exchange of DNA parts.

Patron, N. J., Orzaez, D., Marillonnet, S., Warzecha, H., Matthewman, C., Youles, M., Raitskin, O., Leveau, A., Farré, G., Rogers, C., Smith, A., Hibberd, J., Webb, A. A., Locke, J., Schornack, S., Ajioka, J., Baulcombe, D. C., Zipfel, C., Kamoun, S., Jones, J. D., Kuhn, H., Robatzek, S., Van Esse, H. P., Sanders, D., Oldroyd, G., Martin, C., Field, R, O'Connor, S., Fox S., Wulff, B., Miller, B., Breakspear, A., Radhakrishnan, G., Delaux, P. M., Loqué,, D., Granell, A., Tissier, A., Shih, P., Brutnell, T. P., Quick, W. P., Rischer, H., Fraser, P. D., Aharoni, A., Raines, C., South, P. F., Ané, J. M., Hamberger, B. R., Langdale, J., Stougaard, J., Bouwmeester, H., Udvardi, M., Murray, J. A., Ntoukakis, V., Schäfer, P., Denby, K., Edwards, K. J., Osbourn, A., Haseloff, J. (2015) New Phytol. 208, 13-19.

The bHLH transcription factor BIS1 controls the iridoid branch of the monoterpenoid indole alkaloid pathway in Catharanthus roseus.

Van Moerkercke, A., Steensma, P., Schweizer, F., Pollier, J., Gariboldi, I., Payne, R., Vanden Bossche, R., Miettinen, K., Espoz, J., Purnama, P.C., Kellner, F., Seppänen-Laakso, T., O'Connor, S. E., Rischer, H., Memelink, J., Goossens, A. (2015) Proc. Natl. Acad. Sci. USA 112, 8130-8135.

Discovery of a P450-catalyzed step in vindoline biosynthesis: a link between the aspidosperma and eburnamine alkaloids.

Kellner, F., Geu-Flores, F., Sherden, N. H., Brown, S., Courdavault, V., O'Connor, S. E.* (2015) Chem. Commun. 51, 7626-7628.

Genome biology elucidation of plant natural product biosynthesis.

Kellner, F., Kim, J. Clavijo, B. J., Hamilton, J. P., Childs, K. L., Vaillancourt, B., Cepela, J., Steuernagel, B., Clissold, L., McLay, K., Buell, C. R.*, O’Connor, S. E.* (2015) Plant J. 82, 680-692.

De novo production of the plant-derived alkaloid strictosidine in yeast.

Brown, S., Clastre, M., Courdavault, V. O’Connor, S.E.* (2015) Proc. Natl. Acad. Sci. USA 112, 3205-3210.

Discovery and reconstitution of the cycloclavine biosynthetic pathway - enzymatic formation of a cyclopropyl group.

Jakubczyk, D., Caputi, L., Hatsch, A., Nielsen, C. A. F., Diefenbacher, M., Klein, J., Molt, A., Schröder, H., Cheng, J. Z., Naesby, M., O’Connor, S. E.* (2015) Angew. Chem. Int. Ed. Engl. 54, 5117-5121.

Unlocking the diversity of alkaloids in Catharanthus roseus: nuclear localization suggests metabolic channeling in secondary metabolism.

Stavrinides, A., Tatsis, E.C., Foureau, E., Caputi, L., Kellner, F., Courdavault, V.,* O'Connor, S.E.* (2015) Chem. Biol. 19, 336-341.

Iridoid synthase activity is common among the plant progesterone 5β-reductase family.

Munkert, J., Pollier, J., Miettinen, K., Van Moerkercke, A., Payne, R., Müller-Uri, F., Burlat, V., O'Connor, S.E., Memelink, J., Kreis, W., Goossens, A. (2015) Mol. Plant 8, 136-152.

Conversion of substrate analogs suggests a Michael cyclization in iridoid biosynthesis.

Lindner, S., Geu-Flores, F., Bräse, S., Sherden, N. H.*, O'Connor, S. E.* (2014) Chem. Biol. 21, 1452-1456.

Growing the future: synthetic biology in plants.

O'Connor, S. E, Brutnell, T. P. (2014) Curr. Opin. Plant Biol. 19, iv-v.

The key ergot alkaloid intermediate chanoclavine-I produced in yeast (Saccharomyces cerevisiae) by the combined action of EasC and EasE from Aspergillus japonicus.

Nielsen, C. A. F., Folly, C., Hatsch, A., Molt, A., Schröder, H., O’Connor, S. E., Naesby, M. (2014) Microb Cell Fact. 13, 95.

Biosynthesis of the ergot alkaloids.

Jakubczyk, D., Cheng, J. Z., O'Connor, S. E. (2014) Nat. Prod. Rep. 31, 1328-1338.

A pair of tabersonine 16-hydroxylases initiates the synthesis of vindoline in an organ-dependent manner in Catharanthus roseus.

Besseau, S., Kellner, F., Lanoue, A., Thamm, A. M., Salim, V., Schneider, B., Geu-Flores, F., Höfer, R., Guirimand, G., Guihur, A., Oudin, A., Glevarec, G., Foureau, E., Papon, N., Clastre, M., Giglioli-Guivarc'h, N., St-Pierre, B, Werck-Reichhart, D., Burlat, V., De Luca, V., O'Connor, S. E., Courdavault, V. (2013) Plant Physiol. 163, 1792-1803.

Diversification of monoterpene indole alkaloid analogs through cross-coupling.

Runguphan, W., O'Connor, S. E.* (2013) Org. Lett. 15, 2850-2853.

Recent progress in the metabolic engineering of alkaloids in plant systems.

Glenn, W. S., Runguphan, W., O'Connor, S. E.* (2013) Curr Opin Biotechnol. 24, 354-365.

Modern methods in plant natural products themed issue.

O'Connor SE, Gibbons S. (2013) Nat. Prod. Rep. 30, 483-484.

Development of transcriptomic resources for interrogating the biosynthesis of monoterpene indole alkaloids in medicinal plant species.

Góngora-Castillo, E., Childs, K. L., Fedewa, G., Hamilton, J. P., Liscombe, D. K., Magallanes-Lundback, M., Mandadi, K. K., Nims, E., Runguphan, W., Vaillancourt, B., Varbanova-Herde, M., Dellapenna, D., McKnight, T. D., O'Connor, S., Buell, C. R. (2012) PLoS One. 7, e52506.

An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis.

Geu-Flores, F., Sherden, N. H., Courdavault, V., Burlat, V., Glenn, W. S., Wu, C., Nims, E., Cui, Y., O’Connor, S. E.* (2012) Nature, 492, 138-142.

Plant gene clusters and opiates.

DellaPenna D., O'Connor S. E. (2012) Science 336, 1648-1649.

Recent progress in the metabolic engineering of alkaloids in plant systems.

Glenn, W. S., Runguphan, W., O'Connor, S. E.* (2012) Curr Opin Biotechnol. 24, 354-365.

Redesign of a dioxygenase in morphine biosynthesis.

Glenn, W. S., Runguphan, W., O’Connor, S. E.* (2012) Chem. Biol. 19, 674-678.

Biocatalytic production of tetrahydroisoquinolines.

Ruff, B. M. Brase, S., O’Connor, S. E.* (2012) Tetrahedron Lett. 53, 1071-1074.

Strategies for engineering plant natural products: the iridoid-derived monoterpene indole alkaloids of Catharanthus roseus.

O'Connor S. E. (2012) Meth. Enzymology 515 189-206.

Alkaloids.

O'Connor, S. E.

Edited by: Civjan, Natanya

Natural Products in Chemical Biology (2012), 209-237.

The impact of structural biology on alkaloid biosynthesis research.

Panjikar, S., Stoeckigt, J., O'Connor, S., Warzecha, H.

Natural Product Reports (2012), 29(10), 1176-1200.

Reengineering a tryptophan halogenase to preferentially chlorinate a direct alkaloid precursor.

Glenn, W., Nims, N. E., O'Connor, S. E.* (2011) J. Am. Chem. Soc. 133, 19346-19349.

The evolution of function in strictosidine synthase-like proteins.

Hicks, M. A., Barber II, A. E., Giddings, L. A., O’Connor, S. E., Babbitt P. C. (2011) Proteins. 79, 3082-3098.

A virus-induced gene silencing approach to understanding alkaloid metabolism in Catharanthus roseus.

Liscombe, D. K., O’Connor, S. E.* (2011) Phytochemistry. 72, 1969-1977.

Ergot cluster-encoded catalase is required for synthesis of chanoclavine-I in Aspergillus fumigatus.

Goetz, K. A., Coyle, C. M., Cheng, J. Z., O’Connor, S. E., Panaccione, D. M. (2011) Curr. Gen. 57, 201-211.

A stereoselective hydroxylation step of alkaloid biosynthesis in Catharanthus roseus.

Giddings, L. A., Liscombe, D. K., Hamilton, J. P., Childs, K. L., DellaPenna, D., Buell, C. R., O’Connor, S. E.* (2011) J. Biol. Chem. 286, 16751-16757.

Integrating carbon-halogen bond formation into medicinal plant metabolism.

Runguphan, W., Xudong, Q., O’Connor, S. E.* (2010) Nature 468, 461-464.

A homolog of tocopherol C-methyltransferases catalyzes N-methylation in anticancer alkaloid biosynthesis.

Liscombe, D. K. Usera, A. R., O’Connor, S. E.* (2010) Proc. Natl. Acad. Sci. USA 107, 18793-18798.

Controlling a structural branch point in ergot alkaloid biosynthesis.

Cheng, J. Z., Coyle, C. M., Panaccione, D. M., O’Connor, S. E.* (2010) J. Am. Chem. Soc. 132, 12835-12837.

Biocatalytic asymmetric formation of tetrahydro-beta-carbolines.

Bernhardt, P., Usera, A.R., O’Connor, S.E.* (2010) Tetrahedron Lett. 51, 4400-4402.

An old yellow enzyme required for ergot alkaloid biosynthesis in Aspergillus fumigatus and its role at the branch point between A. fumigatus and Claviceps purpurea ergot alkaloid pathways.

Coyle, C. M., Cheng, J. Z., O’Connor, S. E., Panaccione, D. M. (2010) App. Environ. Microbiol. 76, 3898-3903.

A role for old yellow enzyme in ergot alkaloid biosynthesis.

Cheng, J. Z., Coyle, C. M., Panaccione, D. M., O’Connor, S. E.* (2010) J. Am. Chem. Soc. 132, 1776-1777.

“Alkaloids” in Comprehensive Natural Products II

O’Connor, S. Edited by E. L. Mander, H.-W. Lui, Elsevier: Oxford, 2010; Vol. 1, pp. 977–1007.

Synthesis and biochemical evaluation of des-vinyl secologanin aglycones with alternate stereochemistry.

Bernhardt, P., O'Connor, S. E.* (2009) Tetrahedron Lett. 50, 7118-7120.

Aza-tryptamine substrates in monoterpene indole alkaloid biosynthesis.

Lee, H.-Y., Yerkes, N., O’Connor, S.E.* (2009) Chem. Biol. 16, 1225-1229.

Silencing of tryptamine biosynthesis for production of unnatural alkaloids in plant culture.

Runguphan, W. Maresh, J. J., O’Connor, S. E.* (2009) Proc. Natl. Acad. Sci. USA 106, 13673-13678.

Chemo-enzymatic synthesis of heteroyohimbine alkaloid stereoisomers.

Bernhardt, P., Yerkes, N., O’Connor, S. E.* (2009) Org. Biomol. Chem. 7, 4166-4168.

Mechanistic advances in plant natural product enzymes.

Usera, A.R., O'Connor, S.E.* (2009) Curr. Opin. Chem. Biol. 13, 485-491.

Opportunities in metabolic engineering to enable scalable alkaloid production.

Leonard, E., Runguphan, W., O’Connor, S., Prather, K. J. (2009) Nat. Chem. Biol. 5, 292-300.

Opportunities for enzyme engineering in natural product biosynthesis.

Bernhardt, P., O’Connor, S. E.* (2009) Curr. Opin. Chem. Biol. 13, 35-42.

Metabolic reprogramming of periwinkle plant culture.

Runguphan, W., O’Connor, S. E.* (2009) Nat. Chem. Biol. 5, 151-153.

Synthesis of 4-, 5-, 6- and 7-azido tryptamines.

Friedrich, A., Brase, S., O’Connor, S. E.* (2009) Tetrahedron Lett. 50, 75-76.

Elucidation of natural product pathways in plants.

O’Connor, S. E. (2009) for "Plant-derived natural products; Synthesis, function and application" Springer, A. E. Osbourn, V. Lanzotti, Ed.

Bypassing stereoselectivity in the early steps of alkaloid biosynthesis.

Bernhardt, P., Yerkes, N., O'Connor, S. E.* (2009) Org. Biomol. Chem. 7, 4166-4168.

Strictosidine Synthase: Mechanism of a Pictet-Spengler catalyzing enzyme.

Maresh, J., Giddings, L. A., Friedrich, A., Loris, E. A., Panjikar, S., Stockigt, J.*, Peters, B.*, O’Connor, S. E.* (2008) J. Am. Chem. Soc. 130, 710-723.

Substrate specificity and diastereoselectivity of strictosidine glucosidase.

Yerkes, N., Wu, J., McCoy, E., Galan, M. C., Chen, S., O’Connor, S. E.* (2008) Bioorg. Med. Chem. Lett. 18, 3095-3098.

Alkaloid Biosynthesis.

O’Connor, S. E. (2008) Encyclopedia of Chemical Biology. WileyBlackwell, T. Begley Ed.

Natural products from plant cell culture.

McCoy, E., O’Connor, S. E.* (2008) Prog Drug Res. 65, 331-70.

Chemoselective derivatization of unnatural alkaloids in periwinkle.

Galan, M. C., McCoy, E., O'Connor, S. E.* (2007) Chem. Comm. 3249-3251.

Rapid identification of enzyme variants for reengineered alkaloid biosynthesis in periwinkle.

Bernhardt, P., McCoy, E., O’Connor, S. E.* (2007) Chem. Biol. 14, 888-897.

Redesign of a central enzyme in alkaloid biosynthesis.

Chen, S., Galan, M. C., Carla Coltharp, O'Connor, S. E.* (2006) Chem. Biol. 13, 1137-1141.

Directed biosynthesis of alkaloid analogs in the medicinal plant Catharanthus roseus.

McCoy, E., O'Connor, S. E.* (2006) J. Am. Chem. Soc. 128, 14276-14277.

Chemistry and biology of terpene indole alkaloid biosynthesis.

O'Connor, S. E.*, Maresh, J. M. (2006) Nat. Prod. Rep. 23, 532-547.

Semisynthesis of secologanin derivatives.

Galan, M. C., O'Connor, S. E.* (2006) Tetrahedron Lett. 47, 1563-1565.

Substrate specificity of strictosidine synthase.

McCoy, E., Galan, M. C., O'Connor, S. E.* (2006) Bioorg. Med. Chem. Lett. 16, 2475-2478.

Terpene indole alkaloid biosynthesis.

O'Connor, S. E.*, McCoy, E. M. (2006) Rec. Adv. Phytochem. 40, 1-22.

publications prior to 2005:

Cryptic chlorination a non-haem iron enzyme during cyclopropyl amino acid biosynthesis.

Vaillancourt, F. H., Yeh, E., Vosburg, D. A., O'Connor, S. E., Walsh, C. T. (2005) Nature 436, 1191-1194.

Mass Spectrometric Interrogation of Thioester-Bound Intermediates in the Initial Stages of Epothilone Biosynthesis.

Hicks, L. M.; O'Connor, S. E.; Mazur, M. T., Walsh, C. T., Kelleher, N. L. (2004) Chem. Biol. 11, 327-335.

Aureolic acids: Similar antibiotics with different biosynthetic gene clusters.

O'Connor, Sarah (2004) Chem. Biol. 11, 8-10.

Characterization of CmaA, an adenylation-thiolation didomain enzyme involved in the biosynthesis of coronatine.

Couch, R., O'Connor, S. E., Seidle, H., Walsh, C. T., Parry, R. (2004) J. Bacteriol. 186, 35-42.

Biosynthesis of epothilone intermediates with alternate starter units: Engineering polyketide-nonribosomal interfaces.

O'Connor, S. E., Walsh, C. T., Liu, F. (2003) Angew. Chem. Intnl. Ed. (2003), 42, 3917-3921.

Polyketide-nonribosomal peptide epothilone antitumor agents: the EpoA, B, C subunits.

Walsh, Christopher T.; O'Connor, Sarah E.; Schneider, Tanya L. (2003) J. Ind. Microbiol. Biotechnol. 30, 448-455.

Utilization of Alternate Substrates the First Three Modules of the Epothilone Synthetase Assembly Line.

Schneider, T. L., Walsh, C. T., O'Connor, S. E. (2002) J. Am. Chem. Soc. 124, 11272-11273.

Enzymatic assembly of epothilones: the EpoC subunit and reconstitution of the EpoA-ACP/B/C polyketide and nonribosomal peptide interfaces.

O'Connor, S. E., Chen, H., Walsh, C. T. (2002) Biochemistry. 41, 5685-5694.

Formation of β-hydroxy histidine in the biosynthesis of nikkomycin antibiotics.

Chen, H., Hubbard, B. K., O'Connor, S. E., Walsh, C. T. (2002) Chem. Biol. 9, 103-112.

Epothilone biosynthesis: assembly of the methylthiazolylcarboxy starter unit on the EpoB subunit.

Chen, H., O'Connor, S., Cane, D. E., Walsh, C. T.

Chem. Biol. (2001), 8, 899-912.

Aminoacyl-S-Enzyme Intermediates in β-Hydroxylations and α,β-Desaturations of Amino Acids in Peptide Antibiotics.

Chen, H., Thomas, M. G., O'Connor, S. E., Hubbard, B. K., Burkart, M. D., Walsh, C. T. (2001) Biochemistry. 40, 11651-11659.

Probing the Effect of the Outer Saccharide Residues of N-Linked Glycans on Peptide Conformation.

O'Connor, S. E., Pohlmann, J., Imperiali, B., Saskiawan, I., Yamamoto, K. (2001) J. Am. Chem. Soc. 123, 6187-6188.

Effect of N-linked glycosylation on glycopeptide and glycoprotein structure.

Imperiali, Barbara; O'Connor, Sarah E. (1999) Curr. Opin. Chem. Biol. 3, 643-649.

Chemistry and biology of asparagine-linked glycosylation.

Imperiali, B., O'Connor, S. E., Hendrickson, T.,Kellenberger, C. (1999) Pure Appl. Chem. 71, 777-787.

A molecular basis for glycosylation-induced conformational switching.

O'Connor, S. E., Imperiali, B. (1998) Chem. Biol. 5, 427-437.

The conformational basis of asparagine-linked glycosylation.

Imperiali, B., O'Connor, S. E. (1998) Pure Appl. Chem. 70, 33-40.

Conformational Switching Asparagine-Linked Glycosylation.

O'Connor, S. E., Imperiali, B. (1997) J. Am. Chem. Soc. 119, 2295-2296.

Modulation of protein structure and function asparagine-linked glycosylation.

O'Connor, S. E., Imperali, B. (1996) Chem. Biol. 3, 803-812.