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Biocatalytic routes to stereo-divergent iridoids

Author

Listed:
  • Néstor J. Hernández Lozada

    (Max-Planck Institute for Chemical Ecology, Department of Natural Product Biosynthesis)

  • Benke Hong

    (Max-Planck Institute for Chemical Ecology, Department of Natural Product Biosynthesis)

  • Joshua C. Wood

    (Center for Applied Genetic Technologies, University of Georgia)

  • Lorenzo Caputi

    (Max-Planck Institute for Chemical Ecology, Department of Natural Product Biosynthesis)

  • Jérôme Basquin

    (Max-Planck Institute for Biochemistry, Department of Structural Cell Biology)

  • Ling Chuang

    (Max-Planck Institute for Chemical Ecology, Department of Natural Product Biosynthesis)

  • Maritta Kunert

    (Max-Planck Institute for Chemical Ecology, Department of Natural Product Biosynthesis)

  • Carlos E. Rodríguez López

    (Max-Planck Institute for Chemical Ecology, Department of Natural Product Biosynthesis)

  • Chloe Langley

    (Max-Planck Institute for Chemical Ecology, Department of Natural Product Biosynthesis)

  • Dongyan Zhao

    (Center for Applied Genetic Technologies, University of Georgia)

  • C. Robin Buell

    (Center for Applied Genetic Technologies, University of Georgia)

  • Benjamin R. Lichman

    (University of York, Department of Biology, Centre for Agricultural Products)

  • Sarah E. O’Connor

    (Max-Planck Institute for Chemical Ecology, Department of Natural Product Biosynthesis)

Abstract

Thousands of natural products are derived from the fused cyclopentane-pyran molecular scaffold nepetalactol. These natural products are used in an enormous range of applications that span the agricultural and medical industries. For example, nepetalactone, the oxidized derivative of nepetalactol, is known for its cat attractant properties as well as potential as an insect repellent. Most of these naturally occurring nepetalactol-derived compounds arise from only two out of the eight possible stereoisomers, 7S-cis-trans and 7R-cis-cis nepetalactols. Here we use a combination of naturally occurring and engineered enzymes to produce seven of the eight possible nepetalactol or nepetalactone stereoisomers. These enzymes open the possibilities for biocatalytic production of a broader range of iridoids, providing a versatile system for the diversification of this important natural product scaffold.

Suggested Citation

  • Néstor J. Hernández Lozada & Benke Hong & Joshua C. Wood & Lorenzo Caputi & Jérôme Basquin & Ling Chuang & Maritta Kunert & Carlos E. Rodríguez López & Chloe Langley & Dongyan Zhao & C. Robin Buell & , 2022. "Biocatalytic routes to stereo-divergent iridoids," Nature Communications, Nature, vol. 13(1), pages 1-13, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32414-w
    DOI: 10.1038/s41467-022-32414-w
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    References listed on IDEAS

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    1. Fernando Geu-Flores & Nathaniel H. Sherden & Vincent Courdavault & Vincent Burlat & Weslee S. Glenn & Cen Wu & Ezekiel Nims & Yuehua Cui & Sarah E. O’Connor, 2012. "An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis," Nature, Nature, vol. 492(7427), pages 138-142, December.
    2. Karel Miettinen & Lemeng Dong & Nicolas Navrot & Thomas Schneider & Vincent Burlat & Jacob Pollier & Lotte Woittiez & Sander van der Krol & Raphaël Lugan & Tina Ilc & Robert Verpoorte & Kirsi-Marja Ok, 2014. "The seco-iridoid pathway from Catharanthus roseus," Nature Communications, Nature, vol. 5(1), pages 1-12, May.
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