EC 188.8.131.52 - (S)-norcoclaurine synthase
IntEnz Enzyme Nomenclature
4-hydroxyphenylacetaldehyde hydro-lyase (adding dopamine)
16176 [IUBMB](4-hydroxyphenyl)acetaldehyde(4-hydroxyphenyl)acetaldehydeName origin: UniProt - CHECKED (C)Formula: C8H8O2
Charge: 0ChEBI compound status: CHECKED (C)dopaminedopamineName origin: UniProt - CHECKED (C)Formula: C8H12NO2
Charge: 1ChEBI compound status: CHECKED (C)<=>(S)-norcoclaurine(S)-norcoclaurineName origin: UniProt - CHECKED (C)Formula: C16H18NO3
Charge: 1ChEBI compound status: CHECKED (C)
The reaction makes a six-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates. The product is the precursor of the benzylisoquinoline alkaloids in plants. The enzyme, formerly known as (S)-norlaudanosoline synthase, will also catalyse the reaction of 4-(2-aminoethyl)benzene-1,2-diol + (3,4-dihydroxyphenyl)acetaldehyde to form (S)-norlaudanosoline, but this alkaloid has not been found to occur in plants.
Links to other databases
A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline reticuline.Liebigs Ann. Chem 555-562 (1990).
(S)-Norcoclaurine is the central intermediate in benzylisoquinoline alkaloid biosynthesis.Phytochemistry 28: 1083-1086 (1989).
Purification and characterization of norcoclaurine synthase. The first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants.J. Biol. Chem. 277: 33878-33883 (2002). [PMID: 12107162]
[EC 184.108.40.206 created 1984, modified 1999]