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 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
ATHAT4G22870 AT4G22880(LDOX)
ALY9305872
CRB17880425
CSAT104718018 104722745 104731205
EUSEUTSA_v10025559mg
BRP103860424 103861341
BNA106375745 106440474 106440807 111214282
BOE106301636 106339986
RSZ108843686 108848981
THJ104813007
CPAP110817557
CIT102577958
CICCICLE_v10020815mg
PVY116143357
MINC123204061 123211400
TCC18606417(ANS)
GRA105792153
GHI107926986 107930062 107936429
GAB108461632 108470207
DZI111286882 111289745 111315491
EGR104441822
GMX100801148(ANS3) 547615(ANS2)
GSJ114374275 114424222
PVUPHAVU_002G152700g
VRA106777796
VAR108335234
VUN114173327
CCAJ109799788
APRC113870014
MTRMTR_5g011250
CAM101511289
LJALj2g3v2002950.1(Lj2g3v2002950.1) Lj4g3v1287330.1(Lj4g3v1287330.1)
ADU107488173
AIP107642984
AHF112749557 112800850
LANG109332918
FVE101308284
RCN112179310
PPER18777055
PMUM103337372
PAVI110747768
PDUL117626968
MDM103437326 103437327
PXB103952863
ZJU107429214 107430155 107430385 107430392 107433556
MNT21405925
RCU8272490
JCU105645898
HBR110640000 110651918 110652792
MESC110628286
POP7465826 7490928
PEU105128970 105132195
PALZ118028545 118033651
JRE109010746
QSU111989281
QLO115972360
TWL119980654 119986510
VVI100233142(LDOX)
VRI117904624
SLY101251607
SPEN107027946
SOT102577696(ANS) 102598323(ANS)
CANN107866341
NTA107778118(ANS2) 107819370(ANS1)
NSY104225943
NTO104098957
NAU109212376
INI109168138(ANS)
ITR116000893
SIND105156784
OEU111368826
EGT105967384
SSPL121767670 121771996 121788881
HAN110935543 110935544
ECAD122599614
CCAV112500337
DCR108209615
CSIN114274940 114288034
BVG104892380
SOE110784326
CQI110702537 110719267
NNU104596228 104596229
TSS122668128 122668955
PSOM113275014 113304591
NCOL116249327 116260841
OSA4325716 4341576
DOSAOs01t0372500-00(Os01g0372500) Os06t0626700-00(Os06g0626700)
OBR102706901 121053936
ATS109756683
TDC119314263 119324987 119368967
TAES123042897 123129885 123133050 123140655
TUA125516214
SBI8074150
ZMA100127010
SITA101754899
SVS117850090
PVIR120705980
PHAI112888327
PDA103696959 103702795
EGU105035842 105054281
MUS103983889
DCT110103723
PEQ110019740
AOF109849442
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

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