KEGG   ENZYME: 1.14.11.61
Entry
EC 1.14.11.61               Enzyme                                 
Name
feruloyl-CoA 6-hydroxylase
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
Sysname
feruloyl-CoA,2-oxoglutarate:oxygen oxidoreductase (6-hydroxylating)
Reaction(IUBMB)
trans-feruloyl-CoA + 2-oxoglutarate + O2 = trans-6-hydroxyferuloyl-CoA + succinate + CO2 [RN:R11549]
Reaction(KEGG)
R11549
Substrate
trans-feruloyl-CoA [CPD:C00406];
2-oxoglutarate [CPD:C00026];
O2 [CPD:C00007]
Product
6-hydroxyferuloyl-CoA [CPD:C21459];
succinate [CPD:C00042];
CO2 [CPD:C00011]
Comment
Requires iron(II) and ascorbate. The product spontaneously undergoes trans-cis isomerization and lactonization to form scopoletin, liberating CoA in the process. The enzymes from the plants Ruta graveolens and Ipomoea batatas also act on trans-4-coumaroyl-CoA. cf. EC 1.14.11.62, trans-4-coumaroyl-CoA 2-hydroxylase.
History
EC 1.14.11.61 created 2019
Pathway
ec00999  Biosynthesis of various plant secondary metabolites
ec01110  Biosynthesis of secondary metabolites
Orthology
K06892  feruloyl-CoA 6-hydroxylase
K23378  feruloyl-CoA 6-hydroxylase / trans-4-coumaroyl-CoA 2-hydroxylase
Genes
ATH: AT1G55290 AT3G13610
ALY: 9318972 9321041
CRB: 17893417
CSAT: 104742969 104745611 104765146 104778096
EUS: EUTSA_v10021003mg
BRP: 103842722 103859525 103870109
BNA: 106345852 106351698 106387021 106395905 106440607 106452295
BOE: 106326584 106334207 106343388
RSZ: 108805589 108807602 108856971 108860815 130512442
THJ: 104810332 104811207 104822670
CPAP: 110809597
CIT: 102611531 102611821 102612308 102613413
CIC: CICLE_v10015700mg CICLE_v10015715mg CICLE_v10017524mg CICLE_v10017914mg CICLE_v10018321mg CICLE_v10018343mg CICLE_v10029948mg
PVY: 116139532 116145953
MINC: 123208605 123208607
TCC: 18589593 18590016
GRA: 105781174 105781207 105781216 105782099 105792686 105793736 105799341
GHI: 107891457 107909062 107911341 107911342 107912965 107919558 107919564 107943772 107945535 121204738 121204739 121204740
GAB: 108453468 108457145 108463405 108463460 108463463 108469299 108469339 108469473
HSYR: 120121434 120123198 120123217 120129179 120142046 120144265 120144266
DZI: 111277730 111277731 111293995 111294252 111294332 111294334 111294335 111303902 111304032
GMX: 100527581 100777556 100820326(F6'H1)
GSJ: 114397605 114406404 114418863
PVU: PHAVU_006G023200g PHAVU_006G023300g PHAVU_010G036100g
VRA: 106773844
VAR: 108347270
VUN: 114167306 114186835
VUM: 124822420 124840375
CCAJ: 109807179 109818965
APRC: 113854989 113855375 113856319
MTR: 11413539 25488887
TPRA: 123906175 123910291
LJA: Lj3g3v0652730.1(Lj3g3v0652730.1) Lj6g3v1007880.2(Lj6g3v1007880.2)
ADU: 107472881
AIP: 107615018 107616891
AHF: 112717830 112775183 112777938
LANG: 109363590
PCIN: 129290037 129303332
QSA: O6P43_003828 O6P43_020930 O6P43_020932
FVE: 101291326
RCN: 112164437 112168261
PPER: 18772442
PMUM: 103318655 103331402
PDUL: 117633030
MDM: 103423180
MSYL: 126602911
PXB: 103937496
ZJU: 107410478 107415011 107415012 107415053 107415055 125421938 132803448
MNT: 112090580 112091386 112091846 112092533 112092542 112093530 112095114 21412228 21412376
CSAV: 115710001 115719386
CSV: 101214138
MCHA: 111021233
RCU: 8282975 8282976 8282977 8282978
JCU: 105631594 105631595 105631596 105631723 105637198
HBR: 110642752 110642753 110642754 110642760 110646506 110649460 110652136 110653324 110653328
MESC: 110618463 110619142 110619678 110625121 110625127 110625140 110625159
POP: 112326160 7483255
PEU: 105115498 105142340 105142343
PALZ: 118027905 118027908 118055560
JRE: 108988663 109000614
CILL: 122292889 122294945
CAVE: 132164422 132164540
QSU: 111987312 111991061 111991086 112010742 112032284 112032285 112032288
QLO: 115975208 115975298 115975380 115975550 115975625 115975752 115981013 115981027 115982079 115994543
TWL: 119980108 119983035 120014269 120014278
VVI: 100251923 100257056
VRI: 117916436 117917161
SLY: 101261369 101262487 101265061 101266300 101266599 101266903
SPEN: 107004343 107004359 107004745 107004747 107029794
SOT: 102586708 102588955 102589603 102589939 102590254 102590589 102590939 102596149 102602524 107058105 107058705 107058802
SSTN: 125845134 125845135 125845136 125845137 125845138 125845701 125846948 125850401 125868939 125869050 125869070 125873869 125873870
SDUL: 129884319 129885041 129904128
CANN: 107848279 107848763
LBB: 132600751 132600753 132604627 132604630 132617624 132623405 132628413 132629292 132629402
NTA: 107763182 107770966 107784295 107785648 107787977 107788458 107796566 107803881 107810699
NSY: 104211447 104215338 104215878 104215879 104222156 104245046
NTO: 104085679 104085681 104086193 104106751 104106843 104106844 104111996
NAU: 109226105 109228288 109232742 109232743 109235784 109239160 109239161
INI: 109152302 109152304 109152305 109152306 109152436 109152437 109159769 109160283 109160284 109160285 109160335 109160336 109192759 109192940
ITR: 116003962 116004157 116004252 116005043 116014693 116014694 116014695 116024801 116024932 116025013 116025703 116025820 116026105 116026336
SIND: 105170982
OEU: 111401066 111405833 111407362 111412305
SMIL: 131000327
HAN: 110887178 110890716 110898740 110901341 110903006 110903519 110927168
ECAD: 122582825 122585276 122585606 122598353
LSV: 111882077 111882078 111890219 111919843 111919866 111919868 111919869
CCAV: 112520303 112522132
DCR: 108198298 108198303 108199747 108226415
CSIN: 114273986
RVL: 131315337
AEW: 130785849 130785871
BVG: 104889861
SOE: 110782747 110790461 110792289 110804615
CQI: 110715086 110715111 110715271 110716896 110724886 110730548 110730632
ATRI: 130815127 130823945
MOF: 131148463
NNU: 104612098
TSS: 122652612
 » show all
Reference
1  [PMID:18547395]
  Authors
Kai K, Mizutani M, Kawamura N, Yamamoto R, Tamai M, Yamaguchi H, Sakata K, Shimizu B
  Title
Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana.
  Journal
Plant J 55:989-99 (2008)
DOI:10.1111/j.1365-313X.2008.03568.x
  Sequence
[ath:AT3G13610 AT1G55290]
Reference
2  [PMID:19004461]
  Authors
Bayoumi SA, Rowan MG, Blagbrough IS, Beeching JR
  Title
Biosynthesis of scopoletin and scopolin in cassava roots during post-harvest physiological deterioration: the E-Z-isomerisation stage.
  Journal
Phytochemistry 69:2928-36 (2008)
DOI:10.1016/j.phytochem.2008.09.023
Reference
3  [PMID:22168819]
  Authors
Vialart G, Hehn A, Olry A, Ito K, Krieger C, Larbat R, Paris C, Shimizu B, Sugimoto Y, Mizutani M, Bourgaud F
  Title
A 2-oxoglutarate-dependent dioxygenase from Ruta graveolens L. exhibits p-coumaroyl CoA 2'-hydroxylase activity (C2'H): a missing step in the synthesis of umbelliferone in plants.
  Journal
Plant J 70:460-70 (2012)
DOI:10.1111/j.1365-313X.2011.04879.x
Reference
4  [PMID:22169019]
  Authors
Matsumoto S, Mizutani M, Sakata K, Shimizu B
  Title
Molecular cloning and functional analysis of the ortho-hydroxylases of p-coumaroyl coenzyme A/feruloyl coenzyme A involved in formation of umbelliferone and scopoletin in sweet potato, Ipomoea batatas (L.) Lam.
  Journal
Phytochemistry 74:49-57 (2012)
DOI:10.1016/j.phytochem.2011.11.009
  Sequence
[ag:BAL22347]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.11.61
IUBMB Enzyme Nomenclature: 1.14.11.61
ExPASy - ENZYME nomenclature database: 1.14.11.61
BRENDA, the Enzyme Database: 1.14.11.61

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Pathway (4)   
   KEGG PATHWAY (4)   
Chemical substance (6)   
   KEGG COMPOUND (6)   
Chemical reaction (2)   
   KEGG REACTION (1)   
   KEGG RCLASS (1)   
Gene (397)   
   KEGG ORTHOLOGY (2)   
   KEGG GENES (382)   
   RefGene (13)   
Protein sequence (624)   
   UniProt (613)   
   SWISS-PROT (11)   
Protein domain (4)   
   InterPro (4)   
All databases (1037)   

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