KEGG   ENZYME: 1.14.11.19Help
Entry
EC 1.14.11.19               Enzyme                                 

Name
anthocyanidin synthase;
leucocyanidin oxygenase;
leucocyanidin,2-oxoglutarate:oxygen oxidoreductase;
ANS (gene name)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor
BRITE hierarchy
Sysname
(2R,3S,4S)-leucoanthocyanidin,2-oxoglutarate:oxygen oxidoreductase
Reaction(IUBMB)
a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2 = an anthocyanidin + succinate + CO2 + 2 H2O (overall reaction) [RN:R05723 R07366];
(1a) a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2 = a (4S)- 2,3-dehydroflavan-3,4-diol + succinate + CO2 + H2O;
(1b) a (4S)- 2,3-dehydroflavan-3,4-diol = an anthocyanidin + H2O
Reaction(KEGG)
Substrate
(2R,3S,4S)-leucoanthocyanidin [CPD:C21418];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007];
(4S)- 2,3-dehydroflavan-3,4-diol
Product
anthocyanidin [CPD:C02003];
succinate [CPD:C00042];
CO2 [CPD:C00011];
H2O [CPD:C00001];
(4S)- 2,3-dehydroflavan-3,4-diol
Comment
The enzyme requires Fe(II) and ascorbate. It is involved in the pathway by which many flowering plants make anthocyanin flower pigments (glycosylated anthocyandins). The enzyme hydroxylates the C-3 carbon, followed by a trans diaxial elimination, forming a C-2,C-3 enol. The product loses a second water molecule to form anthocyanidins. When assayed in vitro, non-enzymic epimerization of the product can lead to formation of dihydroflavanols. Thus when the substrate is leucocyanidin, a mixture of (+)-taxifolin and (+)-epitaxifolin are formed. The enzyme can also oxidize the formed (+)-taxifolin to quercetin (cf. EC 1.14.11.23, flavonol synthase) [2,3].
History
EC 1.14.11.19 created 2001, modified 2017
Pathway
Flavonoid biosynthesis
Metabolic pathways
Biosynthesis of secondary metabolites
Orthology
K05277  
leucoanthocyanidin dioxygenase
Genes
ATH: 
ALY: 
CRB: 
EUS: 
BRP: 
BNA: 
BOE: 
THJ: 
CIT: 
CIC: 
TCC: 
GRA: 
GHI: 
EGR: 
GMX: 
100801148(ANS) 547615(ANS)
PVU: 
VRA: 
VAR: 
CCAJ: 
MTR: 
CAM: 
ADU: 
AIP: 
LJA: 
Lj2g3v2002950.1(Lj2g3v2002950.1) Lj4g3v1287330.1(Lj4g3v1287330.1)
LANG: 
FVE: 
PPER: 
PMUM: 
MDM: 
PXB: 
ZJU: 
RCU: 
JCU: 
POP: 
POPTR_0001s08410g(POPTRDRAFT_548547) POPTR_0003s11900g(POPTRDRAFT_646527)
VVI: 
100233142(LDOX)
SLY: 
SPEN: 
SOT: 
CANN: 
NTA: 
107778118(ANS2) 107819370(ANS1)
INI: 
SIND: 
BVG: 
NNU: 
OSA: 
4325716(B1045D11.2) 4341576(P0530H05.4)
DOSA: 
Os01t0372500-00(Os01g0372500) Os06t0626700-00(Os06g0626700)
OBR: 
ATS: 
SBI: 
ZMA: 
SITA: 
PDA: 
EGU: 
MUS: 
ATR: 
 » show all
Taxonomy
Reference
1  [PMID:10074715]
  Authors
Saito K, Kobayashi M, Gong Z, Tanaka Y, Yamazaki M.
  Title
Direct evidence for anthocyanidin synthase as a 2-oxoglutarate-dependent oxygenase: molecular cloning and functional expression of cDNA from a red forma of Perilla frutescens.
  Journal
Plant. J. 17 (1999) 181-9.
  Sequence
Reference
2
  Authors
Turnbull, J.J., Sobey, W.J., Aplin, R.T., Hassan, A., Firmin, J.L., Schofield, C.J. and Prescott, A.G.
  Title
Are anthocyanidins the immediate products of anthocyanidin synthase?.
  Journal
Chem. Commun. (2000) 2473-2474.
Reference
3  [PMID:11796114]
  Authors
Wilmouth RC, Turnbull JJ, Welford RW, Clifton IJ, Prescott AG, Schofield CJ
  Title
Structure and mechanism of anthocyanidin synthase from Arabidopsis thaliana.
  Journal
Structure. 10 (2002) 93-103.
  Sequence
[ath:AT4G22880]
Reference
4  [PMID:14552794]
  Authors
Turnbull JJ, Nagle MJ, Seibel JF, Welford RW, Grant GH, Schofield CJ
  Title
The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity.
  Journal
Bioorg. Med. Chem. Lett. 13 (2003) 3853-7.
Reference
5  [PMID:16494872]
  Authors
Wellmann F, Griesser M, Schwab W, Martens S, Eisenreich W, Matern U, Lukacin R
  Title
Anthocyanidin synthase from Gerbera hybrida catalyzes the conversion of (+)-catechin to cyanidin and a novel procyanidin.
  Journal
FEBS. Lett. 580 (2006) 1642-8.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
180984-01-4

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