KEGG   ORTHOLOGY: K05277
Entry
K05277                      KO                                     
Symbol
ANS
Name
anthocyanidin synthase [EC:1.14.20.4]
Pathway
map00941  Flavonoid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00138  Flavonoid biosynthesis, naringenin => pelargonidin
Reaction
R04276  leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
R05036  leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
R05037  leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
R05723  leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
R06540  leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00941 Flavonoid biosynthesis
    K05277  ANS; anthocyanidin synthase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.20  With 2-oxoglutarate as one donor, and the other dehydrogenated
    1.14.20.4  anthocyanidin synthase
     K05277  ANS; anthocyanidin synthase
Other DBs
GO: 0050589
Genes
ATH: AT4G22870 AT4G22880(LDOX)
ALY: 9305872
CRB: 17880425
CSAT: 104718018 104722745 104731205
EUS: EUTSA_v10025559mg
BRP: 103860424 103861341
BNA: 106375745 106440474 106440807 111214282
BOE: 106301636 106339986
RSZ: 108843686 108848981
THJ: 104813007
CPAP: 110817557
CIT: 102577958(ANS)
PVY: 116143357
TCC: 18606417(ANS)
GRA: 105792153
EGR: 104441822
GMX: 100801148(ANS3) 547615(ANS2)
VRA: 106777796
VAR: 108335234
VUN: 114173327
VUM: 124836972
CCAJ: 109799788
APRC: 113870014
MTR: 11436267
TPRA: 123909938
CAM: 101511289
PSAT: 127120691
VVO: 131652417
LJA: Lj2g3v2002950.1(Lj2g3v2002950.1) Lj4g3v1287330.1(Lj4g3v1287330.1)
ADU: 107488173
AIP: 107642984
LANG: 109332918
FVE: 101308284
RCN: 112179310
PPER: 18777055
PMUM: 103337372
PAVI: 110747768
PDUL: 117626968
PXB: 103952863
MNT: 21405925
CSAV: 115716756
RCU: 8272490
JCU: 105645898
MESC: 110628286
JRE: 109010746
CILL: 122281992
CAVE: 132175962
QSU: 111989281
QLO: 115972360
VVI: 100233142(LDOX)
VRI: 117904624
SLY: 101251607
SPEN: 107027946
SOT: 102577696(ANS) 102598323(ANS)
SSTN: 125841259
SDUL: 129889951
CANN: 107866341
LBB: 132634997
NTA: 107778118(ANS2) 107819370(ANS1)
NSY: 104225943
NTO: 104098957
NAU: 109212376
INI: 109168138(ANS)
ITR: 116000893
SIND: 105156784
OEU: 111368826
EGT: 105967384
SMIL: 130994631
APAN: 127243450
ECAD: 122599614
CCAV: 112500337
DCR: 108209615
RVL: 131331854
BVG: 104892380
SOE: 110784326
ATRI: 130827755
MOF: 131164082
DOSA: Os01t0372500-00(Os01g0372500) Os06t0626700-00(Os06g0626700)
ATS: 109756683
TUA: 125516214
LPER: 127311674
LRD: 124664469
SBI: 8074150
ZMA: 100127010
SITA: 101754899
SVS: 117850090
PVIR: 120705980
PHAI: 112888327
MUS: 103983889
DCT: 110103723
PEQ: 110019740
AOF: 109849442
MSIN: 131223565
ATR: 18424242
AG: BAA20143(ANS)
 » show all
Reference
  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
LinkDB

KEGG   ENZYME: 1.14.20.4
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
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 iron(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
ATHAT4G22870 AT4G22880(LDOX)
ALY9305872
CRB17880425
CSAT104718018 104722745 104731205
EUSEUTSA_v10025559mg
BRP103860424 103861341
BNA106375745 106440474 106440807 111214282
BOE106301636 106339986
RSZ108843686 108848981
THJ104813007
CPAP110817557
CIT102577958(ANS)
CICCICLE_v10020815mg
PVY116143357
MINC123204061 123211400
TCC18606417(ANS)
GRA105792153
GHI107926986 107930062 107936429
GAB108461632 108470207
HSYR120139888 120214326
DZI111286882 111289745 111315491
EGR104441822
GMX100801148(ANS3) 547615(ANS2)
GSJ114374275 114424222
PVUPHAVU_002G152700g
VRA106777796
VAR108335234
VUN114173327
VUM124836972
CCAJ109799788
APRC113870014
MTR11436267
TPRA123909938
CAM101511289
PSAT127120691
VVO131652417
LJALj2g3v2002950.1(Lj2g3v2002950.1) Lj4g3v1287330.1(Lj4g3v1287330.1)
ADU107488173
AIP107642984
AHF112749557 112800850
LANG109332918
PCIN129310951 129321358
FVE101308284
RCN112179310
PPER18777055
PMUM103337372
PAVI110747768
PDUL117626968
MDM103437326 103437327
MSYL126615806 126626418
PXB103952863
ZJU107430392 107433556
MNT21405925
CSAV115716756
RCU8272490
JCU105645898
HBR110640000 110651918 110652792
MESC110628286
POP7465826 7490928
PEU105128970 105132195
PALZ118028545 118033651
JRE109010746
CILL122281992
CAVE132175962
QSU111989281
QLO115972360
TWL119980654 119986510
VVI100233142(LDOX)
VRI117904624
SLY101251607
SPEN107027946
SOT102577696(ANS) 102598323(ANS)
SSTN125841259
SDUL129889951
CANN107866341
LBB132634997
NTA107778118(ANS2) 107819370(ANS1)
NSY104225943
NTO104098957
NAU109212376
INI109168138(ANS)
ITR116000893
SIND105156784
OEU111368826
EGT105967384
SSPL121767670 121771996 121788881
SMIL130994631
APAN127243450
HAN110935543 110935544
ECAD122599614
CCAV112500337
DCR108209615
CSIN114274940 114288034
RVL131331854
AEW130765742 130773081 130795865
BVG104892380
SOE110784326
CQI110702537 110719267
ATRI130827755
MOF131164082
NNU104596228 104596229
TSS122668128 122668955
PSOM113275014 113304591
OSA4325716 4341576
DOSAOs01t0372500-00(Os01g0372500) Os06t0626700-00(Os06g0626700)
OBR102706901 121053936
OGL127771278 127775491
ATS109756683
TDC119314263 119324987 119368967
TAES123042897 123129885 123133050 123140655
TUA125516214
LPER127311674
LRD124664469
SBI8074150
ZMA100127010
SITA101754899
SVS117850090
PVIR120705980
PHAI112888327
PDA103696959 103702795
EGU105035842 105054281
MUS103983889
ZOF122018496 122022294
DCT110103723
PEQ110019740
AOF109849442
MSIN131223565
NCOL116249327 116260841
ATR18424242
 » show all
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
LinkDB

KEGG   REACTION: R05036
Entry
R05036                      Reaction                               
Name
leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
Definition
Cyanidin + Succinate + CO2 + 2 H2O <=> Leucocyanidin + 2-Oxoglutarate + Oxygen + H+
Equation
Comment
Leucoanthocyanidin dioxygenase
acidification
Reaction class
RC01114  C05905_C05906
Enzyme
Pathway
rn00941  Flavonoid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.20  With 2-oxoglutarate as one donor, and the other dehydrogenated
    1.14.20.4
     R05036  Cyanidin + Succinate + CO2 + 2 H2O <=> Leucocyanidin + 2-Oxoglutarate + Oxygen + H+
IUBMB reaction hierarchy [BR:br08202]
 1. Oxidoreductase reactions
  1.14.20.4
   R11993  (2R,3S,4S)-Leucoanthocyanidin <=> Anthocyanidin with a 3-hydroxy group
    R05036  Leucocyanidin <=> Cyanidin
Orthology
K05277  anthocyanidin synthase [EC:1.14.20.4]
LinkDB

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