KEGG   ENZYME: 2.3.1.160Help
Entry
EC 2.3.1.160                Enzyme                                 

Name
vinorine synthase
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
BRITE hierarchy
Sysname
acyl-CoA:16-epivellosimine O-acetyltransferase (cyclizing)
Reaction(IUBMB)
acetyl-CoA + 16-epivellosimine = CoA + vinorine [RN:R05876]
Reaction(KEGG)
Substrate
acetyl-CoA [CPD:C00024];
16-epivellosimine [CPD:C11633]
Product
CoA [CPD:C00010];
vinorine [CPD:C11807]
Comment
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.
History
EC 2.3.1.160 created 2002
Pathway
ec00901  Indole alkaloid biosynthesis
ec01110  Biosynthesis of secondary metabolites
Orthology
K12694  vinorine synthase
Reference
1
  Authors
Pfitzner, A., Polz, L. and Stockligt, J.
  Title
Properties of vinorine synthase the Rauwolfia enzyme involved in the formation of the ajmaline skeleton.
  Journal
Z. Naturforsch. C: Biosci. 41 (1986) 103-114.
Reference
2  [PMID:15110860]
  Authors
Bayer A, Ma X, Stockigt J.
  Title
Acetyltransfer in natural product biosynthesis--functional cloning and molecular analysis of vinorine synthase.
  Journal
Bioorg. Med. Chem. 12 (2004) 2787-95.
  Sequence
Reference
3  [PMID:15450182]
  Authors
Ma X, Koepke J, Bayer A, Linhard V, Fritzsch G, Zhang B, Michel H, Stockigt J.
  Title
Vinorine synthase from Rauvolfia: the first example of crystallization and preliminary X-ray diffraction analysis of an enzyme of the BAHD superfamily.
  Journal
Biochim. Biophys. Acta. 1701 (2004) 129-32.
Reference
4  [PMID:15665331]
  Authors
Ma X, Koepke J, Panjikar S, Fritzsch G, Stockigt J.
  Title
Crystal structure of vinorine synthase, the first representative of the BAHD superfamily.
  Journal
J. Biol. Chem. 280 (2005) 13576-83.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 2.3.1.160
IUBMB Enzyme Nomenclature: 2.3.1.160
ExPASy - ENZYME nomenclature database: 2.3.1.160
BRENDA, the Enzyme Database: 2.3.1.160
CAS: 88844-97-7

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