KEGG ORTHOLOGY: K05277

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)

CIC:	CICLE_v10020815mg

PVY:

116143357

MINC:

123204061 123211400

TCC:	18606417(ANS)

GRA:

105792153

GHI:	107926986 107930062 107936429

GAB:	108461632 108470207

HSYR:

120139888 120214326

DZI:	111286882 111289745 111315491

EGR:

104441822

GMX:	100801148(ANS3) 547615(ANS2)

GSJ:	114374275 114424222

PVU:	PHAVU_002G152700g

VRA:

VAR:

VUN:

VUM:

CCAJ:

APRC:

MTR:

TPRA:

CAM:

PSAT:

VVO:

LJA:

ADU:

AIP:

AHF:	112749557 112800850

LANG:

109332918

PCIN:

129310951 129321358

QSA:	O6P43_024255 O6P43_034175

FVE:

RCN:

PPER:

PMUM:

PAVI:

PDUL:

MDM:	103437326 103437327

MSYL:

126615806 126626418

PXB:

103952863

ZJU:	107430392 107433556

MNT:

CSAV:

RCU:

MEAN:

JCU:

HBR:	110640000 110651918 110652792

MESC:

110628286

POP:	7465826 7490928

PEU:	105128970 105132195

PALZ:

JRE:

CILL:

CAVE:

QSU:

QLO:

TWL:	119980654 119986510

VVI:	100233142(LDOX)

VRI:

117904624

SLY:

101251607

SPEN:

107027946

SOT:	102577696(ANS) 102598323(ANS)

SSTN:

SDUL:

CANN:

LBB:

NTA:	107778118(ANS2) 107819370(ANS1)

NSY:

104225943

NTO:

104098957

NAU:

109212376

INI:	109168138(ANS)

ITR:

SIND:

OEU:

EGT:

SSPL:

121767670 121771996 121788881

SMIL:

130994631

SHIS:

125216387

APAN:

127243450

HAN:	110935543 110935544

ECAD:

CCAV:

DCR:

CSIN:

RVL:

AEW:	130765742 130773081 130795865

BVG:

104892380

SOE:

110784326

CQI:	110702537 110719267

ATRI:

130827755

MOF:

131164082

NNU:	104596228 104596229

TSS:	122668128 122668955

PSOM:

113275014 113304591

OSA:	4325716 4341576(ANS2)

OBR:	102706901 121053936

OGL:	127771278 127775491

ATS:

109756683

TDC:	119314263 119324987 119368967

TAES:

123042897 123129885 123133050 123140655

TUA:

LPER:

LRD:

SBI:

ZMA:

SITA:

SVS:

PVIR:

PHAI:

PDA:	103696959 103702795

EGU:	105035842 105054281

MUS:

103983889

ZOF:	122018496 122022294

DCT:

PEQ:

AOF:

MSIN:

NCOL:

ATR:

AG:	BAA20143(ANS)

» show all

Reference

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

[ag:BAA20143]

LinkDB

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)

R11993 > R04276 R05036 R05037;
R11991 R11992;
(other) R05723 R06540 R07366

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

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)

CIC:	CICLE_v10020815mg

PVY:

116143357

MINC:

123204061 123211400

TCC:	18606417(ANS)

GRA:

105792153

GHI:	107926986 107930062 107936429

GAB:	108461632 108470207

HSYR:

120139888 120214326

DZI:	111286882 111289745 111315491

EGR:

104441822

GMX:	100801148(ANS3) 547615(ANS2)

GSJ:	114374275 114424222

PVU:	PHAVU_002G152700g

VRA:

106777796

VAR:

108335234

VUN:

114173327

VUM:

124836972

CCAJ:

109799788

APRC:

113870014

MTR:

11436267

TPRA:

123909938

CAM:

101511289

PSAT:

127120691

VVO:

131652417

LJA:

130741126

ADU:

107488173

AIP:

107642984

AHF:	112749557 112800850

LANG:

109332918

PCIN:

129310951 129321358

QSA:	O6P43_024255 O6P43_034175

FVE:

101308284

RCN:

112179310

PPER:

18777055

PMUM:

103337372

PAVI:

110747768

PDUL:

117626968

MDM:	103437326 103437327

MSYL:

126615806 126626418

PXB:

103952863

ZJU:	107430392 107433556

MNT:

21405925

CSAV:

115716756

RCU:

8272490

MEAN:

126678744

JCU:

105645898

HBR:	110640000 110651918 110652792

MESC:

110628286

POP:	7465826 7490928

PEU:	105128970 105132195

PALZ:

118028545 118033651

JRE:

109010746

CILL:

122281992

CAVE:

132175962

QSU:

111989281

QLO:

115972360

TWL:	119980654 119986510

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

SSPL:

121767670 121771996 121788881

SMIL:

130994631

SHIS:

125216387

APAN:

127243450

HAN:	110935543 110935544

ECAD:

122599614

CCAV:

112500337

DCR:

108209615

CSIN:

114274940 114288034

RVL:

131331854

AEW:	130765742 130773081 130795865

BVG:

104892380

SOE:

110784326

CQI:	110702537 110719267

ATRI:

130827755

MOF:

131164082

NNU:	104596228 104596229

TSS:	122668128 122668955

PSOM:

113275014 113304591

OSA:	4325716 4341576(ANS2)

OBR:	102706901 121053936

OGL:	127771278 127775491

ATS:

109756683

TDC:	119314263 119324987 119368967

TAES:

123042897 123129885 123133050 123140655

TUA:

125516214

LPER:

127311674

LRD:

124664469

SBI:

8074150

ZMA:

100127010

SITA:

101754899

SVS:

117850090

PVIR:

120705980

PHAI:

112888327

PDA:	103696959 103702795

EGU:	105035842 105054281

MUS:

103983889

ZOF:	122018496 122022294

DCT:

110103723

PEQ:

110019740

AOF:

109849442

MSIN:

131223565

NCOL:

116249327 116260841

ATR:

18424242

» 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

[ag:BAA20143]

Reference

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

REACTION: R05036

Entry

R05036                      Reaction

Name

leucocyanidin,2-oxoglutarate:oxygen oxidoreductase

Definition

Cyanidin + Succinate + CO2 + 2 H2O <=> Leucocyanidin + 2-Oxoglutarate + Oxygen + H+

Equation

C05905 + C00042 + C00011 + 2 C00001 <=> C05906 + C00026 + C00007 + C00080

Comment

Leucoanthocyanidin dioxygenase
acidification

Reaction class

RC01114

C05905_C05906

Enzyme

1.14.20.4

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

DBGET integrated database retrieval system