KEGG ENZYME: 1.3.1.128

ENZYME: 1.3.1.128

Entry

EC 1.3.1.128                Enzyme

Name

precondylocarpine acetate reductase;
DPAS (gene name);
dihydroprecondylocarpine acetate synthase

Class

Oxidoreductases;
Acting on the CH-CH group of donors;
With NAD+ or NADP+ as acceptor

Sysname

precondylocarpine acetate:NADP+ oxidoreductase

Reaction(IUBMB)

dehydrosecondine + acetate + NADP+ = precondylocarpine acetate + NADPH + H+ (overall reaction) [RN:R13445];
(1a) dihydroprecondylocarpine acetate + NADP+ = precondylocarpine acetate + NADPH + H+ [RN:R13345];
(1b) dihydroprecondylocarpine acetate (enamine form) = dihydroprecondylocarpine acetate (spontaneous);
(1c) dehydrosecondine + acetate = dihydroprecondylocarpine acetate (enamine form) (spontaneous) [RN:R13376]

Reaction(KEGG)

R13345 R13376 R13445

Substrate

dehydrosecondine;
acetate [CPD:C00033];
NADP+ [CPD:C00006];
dihydroprecondylocarpine acetate [CPD:C22935]

Product

precondylocarpine acetate [CPD:C22934];
NADPH [CPD:C00005];
H+ [CPD:C00080];
dihydroprecondylocarpine acetate [CPD:C22935]

Comment

The enzyme, characterized from the plant Catharanthus roseus (Madagascar periwinkle), participates in a pathway that leads to the production of a number of monoterpene alkaloids, as well as the bisindole alkaloids vinblastine and vincristine, which are used as anticancer drugs. The enzyme forms the iminium ion form of dihydroprecondylocarpine acetate, which spontaneously rearranges and undergoes deacylation, producing dehydrosecodine.

History

EC 1.3.1.128 created 2024

Pathway

ec00901

Indole alkaloid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K27793

dihydroprecondylocarpine acetate 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:ANQ45231]

Reference

2 [PMID:32066966]

Authors

Caputi L, Franke J, Bussey K, Farrow SC, Vieira IJC, Stevenson CEM, Lawson DM, O'Connor SE.

Title

Structural basis of cycloaddition in biosynthesis of iboga and aspidosperma alkaloids.