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  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., et al. (2018). Discovery of a short-chain dehydrogenase from Catharanthus roseus that produces a novel monoterpene indole alkaloid. Chembiochem, 19(9), 940-948. doi:10.1002/cbic.201700621.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0000-C1C3-9 Version Permalink: https://hdl.handle.net/21.11116/0000-0009-CD83-C
Genre: Journal Article

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NMR252s1.pdf (Supplementary material), 6MB
 
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Stavrinides , A. K., Author
Tatsis , E. C., Author
Dang, T.-T., Author
Caputi, Lorenzo1, Author           
Stevenson, C. E. M., Author
Lawson, D. M., Author
Schneider, Bernd2, Author           
O'Connor, Sarah E.1, Author           
Affiliations:
1External Organizations, ou_persistent22              
2Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society, ou_421898              

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 Abstract: Monoterpene indole alkaloids, a large class of plant natural products, derive from the biosynthetic intermediate strictosidine
aglycone. Strictosidine aglycone, which can exist as a variety of
isomers, can be reduced to form numerous different structures. We
have discovered a short chain alcohol dehydrogenase (SDR) from
monoterpene indole alkaloid producing plants (Catharanthus roseus
and Rauvolfia serpentina) that reduce strictosidine aglycone and
produce an alkaloid that does not correspond to any previously
reported compound. Here we report the structural characterization of
this product, which we have named vitrosamine, as well as the crystal
structure of the SDR. This discovery highlights the structural versatility
of the strictosidine aglycone biosynthetic intermediate and expands
the range of enzymatic reactions that SDRs can catalyze. This
discovery further highlights how a sequence-based gene mining
discovery approach in plants can reveal cryptic chemistry that would
not be uncovered by classical natural product chemistry approaches

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 Dates: 2018-032018-03-222018-05-04
 Publication Status: Issued
 Pages: -
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 Rev. Type: -
 Identifiers: Other: NMR252
DOI: 10.1002/cbic.201700621
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Title: Chembiochem
  Other : Chembiochem
Source Genre: Journal
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Publ. Info: Weinheim, Germany : Wiley-VCH
Pages: - Volume / Issue: 19 (9) Sequence Number: - Start / End Page: 940 - 948 Identifier: ISSN: 1439-4227
CoNE: https://pure.mpg.de/cone/journals/resource/110978984568897