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  Inverted stereocontrol of iridoid synthase in snapdragon

Kries, H., Kellner, F., Kamileen, M. O., & O'Connor, S. E. (2017). Inverted stereocontrol of iridoid synthase in snapdragon. Journal of Biological Chemistry, 292(35), 14659-14667. doi:10.1074/jbc.M117.800979.

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 Creators:
Kries, Hajo, Author
Kellner, Franziska, Author
Kamileen, Mohamed Omar, Author
O'Connor, Sarah E.1, Author           
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1External Organizations, ou_persistent22              

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 Abstract: The natural product class of iridoids, found in various species of flowering plants, harbors astonishing chemical complexity. The discovery of iridoid biosynthetic genes in the medicinal plant Catharanthus roseus has provided insight into the biosynthetic origins of this class of natural product. However, not all iridoids share the exact five- to six-bicyclic ring scaffold of the Catharanthus iridoids. For instance, iridoids in the ornamental flower snapdragon (Antirrhinum majus, Plantaginaceae family) are derived from the C7 epimer of this scaffold. Here we have cloned and characterized the iridoid synthase enzyme from A. majus (AmISY), the enzyme that is responsible for converting 8-oxogeranial into the bicyclic iridoid scaffold in a two-step reduction–cyclization sequence. Chiral analysis of the reaction products reveals that AmISY reduces C7 to generate the opposite stereoconfiguration in comparison with the Catharanthus homologue CrISY. The catalytic activity of AmISY thus explains the biosynthesis of 7-epi-iridoids in Antirrhinum and related genera. However, although the stereoselectivity of the reduction step catalyzed by AmISY is clear, in both AmISY and CrISY, the cyclization step produces a diastereomeric mixture. Although the reduction of 8-oxogeranial is clearly enzymatically catalyzed, the cyclization step appears to be subject to less stringent enzyme control.

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 Dates: 2017
 Publication Status: Published in print
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 Identifiers: Other: SOC084
DOI: 10.1074/jbc.M117.800979
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Title: Journal of Biological Chemistry
  Other : J. Biol. Chem.
Source Genre: Journal
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Publ. Info: Baltimore, etc. : American Society for Biochemistry and Molecular Biology [etc.]
Pages: - Volume / Issue: 292 (35) Sequence Number: - Start / End Page: 14659 - 14667 Identifier: ISSN: 0021-9258
CoNE: https://pure.mpg.de/cone/journals/resource/954925410826