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

DOI: 10.1002/cbic.201700621 DOI Help

Authors: Anna K. Stavrinides (John Innes Centre; Institut de Recherche pour le Développement) , Evangelos Tatsis (John Innes Centre) , Thu-Thuy Dang (John Innes Centre) , Lorenzo Caputi (John Innes Centre) , Clare Stevenson (John Innes Centre) , David Lawson (John Innes Centre) , Bernd Schneider (Max Planck Institute for Chemical Ecology) , Sarah O'Connor (Max Planck Institute for Chemical Ecology)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chembiochem

State: Published (Approved)
Published: February 2018
Diamond Proposal Number(s): 9475

Open Access Open Access

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.

Journal Keywords: alkaloid; biosynthesis; natural product; reduction; short chain dehydrogenase

Diamond Keywords: Enzymes

Subject Areas: Chemistry, Biology and Bio-materials


Instruments: I02-Macromolecular Crystallography

Added On: 15/02/2018 08:34

Documents:
cbic.201700621.pdf

Discipline Tags:

Plant science Biotechnology Biochemistry Chemistry Structural biology Engineering & Technology Organic Chemistry Life Sciences & Biotech

Technical Tags:

Diffraction Macromolecular Crystallography (MX)