KEGG ENZYME: 5.5.1.37

ENZYME: 5.5.1.37

Entry

EC 5.5.1.37                 Enzyme

Name

catharanthine synthase;
CS (gene name)

Class

Isomerases;
Intramolecular lyases;
Intramolecular lyases (only sub-subclass identified to date)

Sysname

dehydrosecodine cyclase (catharanthine-forming)

Reaction(IUBMB)

dehydrosecodine = catharanthine [RN:R13347]

Reaction(KEGG)

R13347

Substrate

dehydrosecodine [CPD:C22960]

Product

catharanthine [CPD:C09107]

Comment

The enzyme, characterized from the plant Catharanthus roseus (Madagascar periwinkle), is a carboxylesterase-like cyclase that catalyses a regio- and enantiodivergent [4+2] cycloaddition reaction to generate the iboga scaffold of catharanthine. cf. EC 5.5.1.38, tabersonine synthase.

History

EC 5.5.1.37 created 2024

Pathway

ec00901

Indole alkaloid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K27794

catharanthine synthase

Reference

1 [PMID:29724909]

Authors

Caputi L, Franke J, Farrow SC, Chung K, Payne RME, Nguyen TD, Dang TT, Soares Teto Carqueijeiro I, Koudounas K, Duge de Bernonville T, Ameyaw B, Jones DM, Vieira IJC, Courdavault V, O'Connor SE

Title

Missing enzymes in the biosynthesis of the anticancer drug vinblastine in Madagascar periwinkle.

Journal

Science 360:1235-1239 (2018)
DOI:10.1126/science.aat4100

Sequence

[ag:AVM85920]

Reference

2 [PMID:38319969]

Authors

DeMars MD 2nd, O'Connor SE.

Title

Evolution and diversification of carboxylesterase-like [4+2] cyclases in aspidosperma and iboga alkaloid biosynthesis.