KEGG   ORTHOLOGY: K13382
Entry
K13382                      KO                                     
Symbol
NCS
Name
(S)-norcoclaurine synthase [EC:4.2.1.78]
Pathway
map00950  Isoquinoline alkaloid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00943  Reticuline biosynthesis, dopamine + 4HPAA => (S)-reticuline
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00950 Isoquinoline alkaloid biosynthesis
    K13382  NCS; (S)-norcoclaurine synthase
Enzymes [BR:ko01000]
 4. Lyases
  4.2  Carbon-oxygen lyases
   4.2.1  Hydro-lyases
    4.2.1.78  (S)-norcoclaurine synthase
     K13382  NCS; (S)-norcoclaurine synthase
Other DBs
RN: R04084 R04305
GO: 0050474
Genes
PSOM: 113277377 113326100 113340282
AG: AAR22502(NCS)
Reference
  Authors
Luk LY, Bunn S, Liscombe DK, Facchini PJ, Tanner ME
  Title
Mechanistic studies on norcoclaurine synthase of benzylisoquinoline alkaloid biosynthesis: an enzymatic Pictet-Spengler reaction.
  Journal
Biochemistry 46:10153-61 (2007)
DOI:10.1021/bi700752n
Reference
  Authors
Samanani N, Liscombe DK, Facchini PJ
  Title
Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis.
  Journal
Plant J 40:302-13 (2004)
DOI:10.1111/j.1365-313X.2004.02210.x
  Sequence
LinkDB

KEGG   ENZYME: 4.2.1.78
Entry
EC 4.2.1.78                 Enzyme                                 
Name
(S)-norcoclaurine synthase;
(S)-norlaudanosoline synthase;
4-hydroxyphenylacetaldehyde hydro-lyase (adding dopamine)
Class
Lyases;
Carbon-oxygen lyases;
Hydro-lyases
Sysname
4-hydroxyphenylacetaldehyde hydro-lyase [adding dopamine; (S)-norcoclaurine-forming]
Reaction(IUBMB)
4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O [RN:R04305]
Reaction(KEGG)
R04305;
(other) R04084
Substrate
4-hydroxyphenylacetaldehyde [CPD:C03765];
dopamine [CPD:C03758]
Product
(S)-norcoclaurine [CPD:C06160];
H2O [CPD:C00001]
Comment
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.
History
EC 4.2.1.78 created 1984, modified 1999
Pathway
ec00950  Isoquinoline alkaloid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13382  (S)-norcoclaurine synthase
Genes
PSOM113277377 113326100 113340282
Reference
1
  Authors
Stadler, R., Zenk, M.H.
  Title
A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline reticuline.
  Journal
Liebigs Ann Chem 555-562 (1990)
Reference
2
  Authors
Stadler, R., Kutchan, T.M., Zenk, M.H.
  Title
(S)-Norcoclaurine is the central intermediate in benzylisoquinoline alkaloid biosynthesis.
  Journal
Phytochemistry 28:1083-1086 (1989)
Reference
3  [PMID:12107162]
  Authors
Samanani N, Facchini PJ.
  Title
Purification and characterization of norcoclaurine synthase. The first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants.
  Journal
J Biol Chem 277:33878-83 (2002)
DOI:10.1074/jbc.M203051200
Other DBs
ExplorEnz - The Enzyme Database: 4.2.1.78
IUBMB Enzyme Nomenclature: 4.2.1.78
ExPASy - ENZYME nomenclature database: 4.2.1.78
BRENDA, the Enzyme Database: 4.2.1.78
CAS: 79122-01-3
LinkDB

KEGG   REACTION: R04305
Entry
R04305                      Reaction                               
Name
4-Hydroxyphenylacetaldehyde hydro-lyase (adding dopamine)
Definition
4-Hydroxyphenylacetaldehyde + Dopamine <=> (S)-Norcoclaurine + H2O
Equation
Comment
multi-step reaction
Reaction class
RC01071  C03758_C06160
RC01072  C03765_C06160
Enzyme
Pathway
rn00950  Isoquinoline alkaloid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00943  Reticuline biosynthesis, dopamine + 4HPAA => (S)-reticuline
Orthology
K13382  (S)-norcoclaurine synthase [EC:4.2.1.78]
Other DBs
RHEA: 16176
LinkDB

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