KEGG   ENZYME: 4.1.2.61
Entry
EC 4.1.2.61                 Enzyme                                 

Name
feruloyl-CoA hydratase/lyase;
hydroxycinnamoyl-CoA hydratase lyase;
enoyl-CoA hydratase/aldolase;
HCHL;
ferB (gene name);
couA (gene name)
Class
Lyases;
Carbon-carbon lyases;
Aldehyde-lyases
Sysname
feruloyl-CoA hydro-lyase/vanillin-lyase (acetyl-CoA-forming)
Reaction(IUBMB)
feruloyl-CoA + H2O = vanillin + acetyl-CoA (overall reaction) [RN:R12566];
(1a) feruloyl-CoA + H2O = 3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoyl-CoA [RN:R05772];
(1b) 3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoyl-CoA = vanillin + acetyl-CoA [RN:R05773]
Reaction(KEGG)
Substrate
feruloyl-CoA [CPD:C00406];
H2O [CPD:C00001];
3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoyl-CoA [CPD:C07303]
Product
vanillin [CPD:C00755];
acetyl-CoA [CPD:C00024];
3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoyl-CoA [CPD:C07303]
Comment
The enzyme is a member of the enoyl-CoA hydratase/isomerase superfamily. It catalyses a two-step process involving first the hydration of the double bond of feruloyl-CoA and then the cleavage of the resultant beta-hydroxy thioester by retro-aldol reaction. (E)-caffeoyl-CoA and (E)-4-coumaroyl-CoA are also substrates.
History
EC 4.1.2.61 created 2020 (EC 4.1.2.41 created 2000, incorporated 2020, EC 4.2.1.101 created 2000, incorporated 2020)
Pathway
ec00998  Biosynthesis of various secondary metabolites - part 2
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K18383  feruloyl-CoA hydratase/lyase
Genes
REE: electrica_04643
XCC: XCC0810(fadB)
XCB: XC_3420
XCA: xcc-b100_3542(ech4)
XCP: XCR_0990
XCV: XCV0918(paaF)
XAX: XACM_0864(paaF)
XAC: XAC0883(fadB)
XCI: XCAW_03697(caiD)
XCT: J151_01010
XOM: XOO3520(XOO3520)
XOO: XOO3728(fadB)
XOP: PXO_04626
XOR: XOC_0934
XAL: XALC_3045
XPH: XppCFBP6546_07095(XppCFBP6546P_07095)
PPU: PP_3358
PPF: Pput_2400
PSB: Psyr_2728
PSYR: N018_13590
PPRO: PPC_3628(paaG)
PFS: PFLU_3300
PSES: PSCI_1563(paaG)
PSEM: TO66_18490
PSOS: POS17_3613(paaG)
AVN: Avin_14230(ech)
AVL: AvCA_14230(ech)
AVD: AvCA6_14230(ech)
ACX: Achr_28510(ech)
ACB: A1S_1111
ABY: ABAYE2628(hcaA)
ABN: AB57_1195
ABAZ: P795_11770
ABAU: IX87_05290
ABAA: IX88_07805
ACC: BDGL_000391(hcaA)
ACI: ACIAD1726(hcaA)
AUG: URS_0068
CSA: Csal_0278
HAM: HALO0103
SALN: SALB1_1097
RSO: RSp0225(fca)
RSN: RSPO_m00213(fca)
RSE: F504_3664
BMA: BMAA0629
BMAL: DM55_4800
BMAE: DM78_3189
BMAQ: DM76_3754
BMAI: DM57_12400
BMAF: DM51_4342
BMAZ: BM44_4790
BMAB: BM45_4942
BPS: BPSS0779
BPM: BURPS1710b_A2361(ech)
BPSE: BDL_4061
BPSM: BBQ_5363
BPSU: BBN_4233
BPSD: BBX_5899
BPSH: DR55_4562
BPSA: BBU_5259
BVE: AK36_4870
BCN: Bcen_5223
BCJ: BCAM2793
BCEN: DM39_5052
BCEW: DM40_3360
BCEO: I35_6672
BAM: Bamb_4916
BMU: Bmul_3210
BMK: DM80_4590
BMUL: NP80_3343
BCT: GEM_5614
BCED: DM42_5195
BDL: AK34_5013
BCON: NL30_17810
BUB: BW23_3981
BLAT: WK25_29380
BTEI: WS51_10605
BSEM: WJ12_33825
BPSL: WS57_00300
BMEC: WJ16_32335
BSTG: WT74_32690
BGO: BM43_7003
BUK: MYA_3497
BUL: BW21_6349
PPNO: DA70_11115
PPNM: LV28_19940
PPUL: RO07_14150
PSPU: NA29_22960
PAPI: SG18_13975
AFQ: AFA_15960
DAC: Daci_2758
RSV: Rsl_444
RSW: MC3_02165
MLO: mlr1841
MHUA: MCHK_3418
AVI: Avi_1705(fadB)
RLE: pRL120505(ech)
RLG: Rleg_4811
MET: M446_3478
META: Y590_19210
CCR: CC_2401
CAK: Caul_1132
NAR: Saro_1669
SPHI: TS85_18585
SSAN: NX02_02990
SJP: SJA_C1-02370(menB)
SSY: SLG_07870(ferB2) SLG_25030(ferB)
SPHR: BSY17_3548
BLAS: BSY18_3470
AAY: WYH_03221
ALB: AEB_P1354
SHUM: STHU_10230
AZL: AZL_b03680(paaG)
SEN: SACE_2794
AMYY: YIM_23925
PSEE: FRP1_10310
PAUT: Pdca_42230
AMI: Amir_4116
KAL: KALB_2035
SUS: Acid_0255
SMIZ: 4412673_04091(menB)
 » show all
Reference
1  [PMID:6870241]
  Authors
Pometto AL 3rd, Crawford DL.
  Title
Whole-cell bioconversion of vanillin to vanillic acid by Streptomyces viridosporus.
  Journal
Appl Environ Microbiol 45:1582-5 (1983)
DOI:10.1128/AEM.45.5.1582-1585.1983
Reference
2  [PMID:9611814]
  Authors
Narbad A, Gasson MJ.
  Title
Metabolism of ferulic acid via vanillin using a novel CoA-dependent pathway in a newly-isolated strain of Pseudomonas fluorescens.
  Journal
Microbiology 144 ( Pt 5):1397-405 (1998)
DOI:10.1099/00221287-144-5-1397
Reference
3  [PMID:9461612]
  Authors
Gasson MJ, Kitamura Y, McLauchlan WR, Narbad A, Parr AJ, Parsons EL, Payne J, Rhodes MJ, Walton NJ
  Title
Metabolism of ferulic acid to vanillin. A bacterial gene of the enoyl-SCoA hydratase/isomerase superfamily encodes an enzyme for the hydration and cleavage  of a hydroxycinnamic acid SCoA thioester.
  Journal
J Biol Chem 273:4163-70 (1998)
DOI:10.1074/jbc.273.7.4163
  Sequence
[pfs:PFLU_3300]
Reference
4  [PMID:10543794]
  Authors
Overhage J, Priefert H, Steinbuchel A
  Title
Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199.
  Journal
Appl Environ Microbiol 65:4837-47 (1999)
DOI:10.1128/AEM.65.11.4837-4847.1999
Reference
5  [PMID:18479250]
  Authors
Bennett JP, Bertin L, Moulton B, Fairlamb IJ, Brzozowski AM, Walton NJ, Grogan G
  Title
A ternary complex of hydroxycinnamoyl-CoA hydratase-lyase (HCHL) with acetyl-CoA  and vanillin gives insights into substrate specificity and mechanism.
  Journal
Biochem J 414:281-9 (2008)
DOI:10.1042/BJ20080714
  Sequence
[pfs:PFLU_3300]
Reference
6  [PMID:22328668]
  Authors
Hirakawa H, Schaefer AL, Greenberg EP, Harwood CS
  Title
Anaerobic p-coumarate degradation by Rhodopseudomonas palustris and identification of CouR, a MarR repressor protein that binds p-coumaroyl coenzyme  A.
  Journal
J Bacteriol 194:1960-7 (2012)
DOI:10.1128/JB.06817-11
  Sequence
[rpa:RPA1786]
Reference
7  [PMID:23840666]
  Authors
Yang W, Tang H, Ni J, Wu Q, Hua D, Tao F, Xu P
  Title
Characterization of two Streptomyces enzymes that convert ferulic acid to vanillin.
  Journal
PLoS One 8:e67339 (2013)
DOI:10.1371/journal.pone.0067339
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 4.1.2.61
IUBMB Enzyme Nomenclature: 4.1.2.61
ExPASy - ENZYME nomenclature database: 4.1.2.61
BRENDA, the Enzyme Database: 4.1.2.61

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