KEGG ENZYME: 2.3.1.160

ENZYME: 2.3.1.160

Entry

EC 2.3.1.160                Enzyme

Name

vinorine synthase

Class

Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups

Sysname

acyl-CoA:16-epivellosimine O-acetyltransferase (cyclizing)

Reaction(IUBMB)

acetyl-CoA + 16-epivellosimine = CoA + vinorine [RN:R05876]

Reaction(KEGG)

R05876

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

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 41:103-114 (1986)

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 12:2787-95 (2004)
DOI:10.1016/j.bmc.2004.02.029

Sequence

[ag:CAD89104]

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 1701:129-32 (2004)
DOI:10.1016/j.bbapap.2004.06.011

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 280:13576-83 (2005)
DOI:10.1074/jbc.M414508200

Sequence

[ag:CAD89104]