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  Uncoupled activation and cyclization in catmint reductive terpenoid biosynthesis

Lichman, B. R., Kamileen, M. O., Titchiner, G. R., Saalbach, G., Stevenson, C. E. M., Lawson, D. M., et al. (2019). Uncoupled activation and cyclization in catmint reductive terpenoid biosynthesis. Nature Chemical Biology, 15, 71-79. doi:10.1038/s41589-018-0185-2.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0002-BC45-D Version Permalink: https://hdl.handle.net/21.11116/0000-0009-3BAA-6
Genre: Journal Article

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SOC070.pdf (Publisher version), 2MB
 
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Lichman, Benjamin R., Author
Kamileen, Mohamed O., Author
Titchiner, Gabriel R., Author
Saalbach, Gerhard, Author
Stevenson, Clare E. M., Author
Lawson, David M., Author
O'Connor, Sarah E.1, Author           
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1External Organizations, ou_persistent22              

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 Abstract: Terpene synthases typically form complex molecular scaffolds by concerted activation and cyclization of linear starting materials in a single enzyme active site. Here we show that iridoid synthase, an atypical reductive terpene synthase, catalyzes the activation of its substrate 8-oxogeranial into a reactive enol intermediate, but does not catalyze the subsequent cyclization into nepetalactol. This discovery led us to identify a class of nepetalactol-related short-chain dehydrogenase enzymes (NEPS) from catmint (Nepeta mussinii) that capture this reactive intermediate and catalyze the stereoselective cyclisation into distinct nepetalactol stereoisomers. Subsequent oxidation of nepetalactols by NEPS1 provides nepetalactones, metabolites that are well known for both insect-repellent activity and euphoric effects in cats. Structural characterization of the NEPS3 cyclase reveals that it binds to NAD+ yet does not utilize it chemically for a non-oxidoreductive formal [4 + 2] cyclization. These discoveries will complement metabolic reconstructions of iridoid and monoterpene indole alkaloid biosynthesis.

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 Dates: 2018-11-062018-12-102019-01
 Publication Status: Issued
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 Identifiers: Other: SOC070
DOI: 10.1038/s41589-018-0185-2
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Title: Nature Chemical Biology
  Other : Nat. Chem. Biol.
Source Genre: Journal
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Publ. Info: New York, NY : Nature Pub. Group
Pages: - Volume / Issue: 15 Sequence Number: - Start / End Page: 71 - 79 Identifier: ISSN: 1552-4450
CoNE: https://pure.mpg.de/cone/journals/resource/1000000000021290_1