KEGG   ENZYME: 1.14.19.80
Entry
EC 1.14.19.80               Enzyme                                 
Name
(19E)-geissoschizine oxidase;
GO (gene name);
CYP71D1V1 (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With oxidation of a pair of donors resulting in the reduction of O2 to two molecules of water
Sysname
(19E)-geissoschizine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (akuammicine-forming)
Reaction(IUBMB)
(19E)-geissoschizine + O2 + [reduced NADPH-hemoprotein reductase] = akuammicine + formate + H2O + [oxidized NADPH-hemoprotein reductase] (overall reaction) [RN:R13381];
(1a) (19E)-geissoschizine + O2 + [reduced NADPH-hemoprotein reductase] = 3,17-didehydrostemmadenine + 2 H2O + [oxidized NADPH-hemoprotein reductase] [RN:R13342];
(1b) 3,17-didehydrostemmadenine = 17-dehydropreakuammicine (spontaneous) [RN:R13329];
(1c) 17-dehydropreakuammicine + H2O = 17-dehydropreakuammicine hydrate (spontaneous) [RN:R13382];
(1d) 17-dehydropreakuammicine hydrate = akuammicine + formate (spontaneous) [RN:R13331]
Reaction(KEGG)
Substrate
(19E)-geissoschizine [CPD:C02151];
O2 [CPD:C00007];
[reduced NADPH-hemoprotein reductase];
3,17-didehydrostemmadenine [CPD:C22936];
17-dehydropreakuammicine [CPD:C22922];
H2O [CPD:C00001];
17-dehydropreakuammicine hydrate [CPD:C22961]
Product
akuammicine [CPD:C09025];
formate [CPD:C00058];
H2O [CPD:C00001];
[oxidized NADPH-hemoprotein reductase];
3,17-didehydrostemmadenine [CPD:C22936];
17-dehydropreakuammicine [CPD:C22922];
17-dehydropreakuammicine hydrate [CPD:C22961]
Comment
A cytochrome P-450 (heme-thiolate) enzyme characterized from the plant Catharanthus roseus (Madagascar periwinkle), that participates in the biosynthesis of a number of monoterpene alkaloids, as well as the bisindole alkaloids vinblastine and vincristine. The enzyme generates a nine-carbon ring that contains a nitrogen atom. The direct product of the enzyme, 3,17-didehydrostemmadenine, is unstable, and in the absence of other enzymes becomes akuammicine non-enzymically. However, in the presence of two dehydrogenases it is converted to stemmadenine via 17-dehydrostemmadenine.
History
EC 1.14.19.80 created 2024
Pathway
ec00901  Indole alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K27780  (19E)-geissoschizine oxidase
Reference
1  [PMID:28827772]
  Authors
Tatsis EC, Carqueijeiro I, Duge de Bernonville T, Franke J, Dang TT, Oudin A, Lanoue A, Lafontaine F, Stavrinides AK, Clastre M, Courdavault V, O'Connor SE
  Title
A three enzyme system to generate the Strychnos alkaloid scaffold from a central biosynthetic intermediate.
  Journal
Nat Commun 8:316 (2017)
DOI:10.1038/s41467-017-00154-x
Reference
2  [PMID:29511102]
  Authors
Qu Y, Easson MEAM, Simionescu R, Hajicek J, Thamm AMK, Salim V, De Luca V
  Title
Solution of the multistep pathway for assembly of corynanthean, strychnos, iboga, and aspidosperma monoterpenoid indole alkaloids from 19E-geissoschizine.
  Journal
Proc Natl Acad Sci U S A 115:3180-3185 (2018)
DOI:10.1073/pnas.1719979115
  Sequence
Reference
3  [PMID:37626942]
  Authors
Salim V, Jarecki SA, Vick M, Miller R.
  Title
Advances in Metabolic Engineering of Plant Monoterpene Indole Alkaloids.
  Journal
Biology (Basel) 12:1056 (2023)
DOI:10.3390/biology12081056
Other DBs
ExplorEnz - The Enzyme Database: 1.14.19.80
IUBMB Enzyme Nomenclature: 1.14.19.80
ExPASy - ENZYME nomenclature database: 1.14.19.80
BRENDA, the Enzyme Database: 1.14.19.80
LinkDB

DBGET integrated database retrieval system