KEGG   ENZYME: 1.14.20.4Help
Entry
EC 1.14.20.4                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 the other dehydrogenated
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:R11993];
(1a) a (2R,3S,4S)-leucoanthocyanidin + 2-oxoglutarate + O2 = a (4S)- 2,3-dehydroflavan-3,4-diol + succinate + CO2 + H2O [RN:R11991];
(1b) a (4S)- 2,3-dehydroflavan-3,4-diol = an anthocyanidin + H2O [RN:R11992]
Reaction(KEGG)
Substrate
(2R,3S,4S)-leucoanthocyanidin [CPD:C21418];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007];
(4S)- 2,3-dehydroflavan-3,4-diol [CPD:C21832]
Product
anthocyanidin [CPD:C21381];
succinate [CPD:C00042];
CO2 [CPD:C00011];
H2O [CPD:C00001];
(4S)- 2,3-dehydroflavan-3,4-diol [CPD:C21832]
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 1.14.20.6, flavonol synthase) [2,3].
History
EC 1.14.20.4 created 2001 as EC 1.14.11.19, transferred 2018 to EC 1.14.20.4
Pathway
ec00941  Flavonoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K05277  anthocyanidin synthase
Genes
ATH: AT4G22870 AT4G22880(LDOX)
ALY: ARALYDRAFT_492580
CRB: 17880425
CSAT: 104718018 104722745 104731205 109127199 109131729
EUS: EUTSA_v10025559mg
BRP: 103860424(ANS) 103861341
BNA: 106375745 106440474 106440807 111214282
BOE: 106301636 106339986
THJ: 104813007
CPAP: 110817557
CIT: 102577958
TCC: 18606417(ANS)
GRA: 105792153
EGR: 104441822
GMX: 100801148(ANS3) 547615(ANS2)
VRA: 106777796
VAR: 108335234
CCAJ: 109799788
CAM: 101511289
LJA: Lj2g3v2002950.1(Lj2g3v2002950.1) Lj4g3v1287330.1(Lj4g3v1287330.1)
ADU: 107488173
AIP: 107642984
LANG: 109332918
FVE: 101308284
PPER: 18777055
PMUM: 103337372
PAVI: 110747768
PXB: 103952863
RCU: 8272490
JCU: 105645898
MESC: 110628286
JRE: 109010746
VVI: 100233142(LDOX)
SLY: 101251607
SPEN: 107027946
SOT: 102577696(ANS) 102598323(ANS)
CANN: 107866341
NTA: 107778118(ANS2) 107819370(ANS1)
NSY: 104225943
NTO: 104098957
INI: 109168138(ANS)
SIND: 105156784
OEU: 111368826
CCAV: 112500337
DCR: 108209615
BVG: 104892380
SOE: 110784326
DOSA: Os01t0372500-00(Os01g0372500) Os06t0626700-00(Os06g0626700)
ATS: 109756683(LOC109756683)
SBI: 8074150
SITA: 101754899
MUS: 103983889
DCT: 110103723
PEQ: 110019740
AOF: 109849442
ATR: 18424242
 » 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 17:181-9 (1999)
DOI:10.1046/j.1365-313X.1999.00365.x
  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:2473-2474 (2000)
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 10:93-103 (2002)
DOI:10.1016/S0969-2126(01)00695-5
  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 13:3853-7 (2003)
DOI:10.1016/S0960-894X(03)00711-X
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 580:1642-8 (2006)
DOI:10.1016/j.febslet.2006.02.004
Other DBs
ExplorEnz - The Enzyme Database: 1.14.20.4
IUBMB Enzyme Nomenclature: 1.14.20.4
ExPASy - ENZYME nomenclature database: 1.14.20.4
BRENDA, the Enzyme Database: 1.14.20.4
CAS: 180984-01-4

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