EC 18.104.22.168 - Vinorine synthase
IntEnz Enzyme Nomenclature
24016 [IUBMB]16-epivellosimine16-epivellosimineName origin: UniProt - CHECKED (C)Formula: C19H20N2O
Charge: 0ChEBI compound status: CHECKED (C)acetyl-CoAacetyl-CoAName origin: UniProt - CHECKED (C)Formula: C23H34N7O17P3S
Charge: -4ChEBI compound status: CHECKED (C)=CoACoAName origin: UniProt - CHECKED (C)Formula: C21H32N7O16P3S
Charge: -4ChEBI compound status: CHECKED (C)
The reaction proceeds in two stages. The indole nitrogen of 16-epivellosimine interacts with its aldehyde group giving an hydroxy-substituted new ring. This alcohol is then acetylated. Also acts on gardneral (11-methoxy-16-epivellosimine). Generates the ajmalan skeleton, which forms part of the route to ajmaline.
Links to other databases
Properties of vinorine synthase the Rauwolfia enzyme involved in the formation of the ajmaline skeleton.Z. Naturforsch. C: Biosci. 41: 103-114 (1986).
Acetyltransfer in natural product biosynthesis—--functional cloning and molecular analysis of vinorine synthase.Bioorg. Med. Chem. 12: 2787-2795 (2004). [PMID: 15110860]
Vinorine synthase from Rauvolfia: the first example of crystallization and preliminary X-ray diffraction analysis of an enzyme of the BAHD superfamily.Biochim. Biophys. Acta 1701: 129-132 (2004). [PMID: 15450182]
Crystal structure of vinorine synthase, the first representative of the BAHD superfamily.J. Biol. Chem. 280: 13576-13583 (2005). [PMID: 15665331]
[EC 22.214.171.124 created 2002]