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
ec00996  Biosynthesis of various alkaloids
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K18383  feruloyl-CoA hydratase/lyase
Genes
REEelectrica_04643
XCCXCC0810(fadB)
XCBXC_3420
XCAxcc-b100_3542(ech4)
XCPXCR_0990
XCVXCV0918(paaF)
XAXXACM_0864(paaF)
XACXAC0883(fadB)
XCIXCAW_03697(caiD)
XCTJ151_01010
XCJJ158_01007
XCUJ159_01007
XCNJ169_01006
XCWJ162_01006
XCRJ163_01006
XCMJ164_01006
XCFJ172_01001
XFUXFF4834R_chr08860
XAOXAC29_04495
XOMXOO3520(XOO3520)
XOOXOO3728(fadB)
XOPPXO_04626
XOYAZ54_05255
XORXOC_0934
XOZBE73_19720
XALXALC_3045
XSASB85_14030
XVEBJD12_17330
XPEBJD13_12380
XHRXJ27_10980
XGABI317_05235
XPHXppCFBP6546_07095(XppCFBP6546P_07095)
XVAC7V42_04780
XANAC801_04465
XARXB05_21265
XCZEBN15_03385
XTHG4Q83_17825
XEUXSP_000869
XHDLMG31886_34600
PPUPP_3358
PPFPput_2400
PPWPputW619_2047
PPUTL483_17020 L483_20055
PFVPsefu_4045
PORAPT59_07760
PSTPSPTO_2944
PSBPsyr_2728
PSYRN018_13590
PSPPSPPH_2433
PSAVPSA3335_15695
PAMGBKM19_016455
PAVLBKM03_14265
PVDCFBP1590__2836
PCABJGS08_12745
PPRCPFLCHA0_c35190
PPROPPC_3628(paaG)
PFEPSF113_2659
PFSPFLU_3300
PPZH045_05705
PTVAA957_00730
PCGAXG94_01490
PVRPverR02_12195
PAZOAYR47_20520
PLULFOB45_07565
PBAPSEBR_a3136
PBCCD58_14285
PSKU771_11770
PCHEY04_17960
PCZPCL1606_25820
PCPJM49_12990
PFZAV641_10360
PSESPSCI_1563(paaG)
PSEMTO66_18490
PSOSPOS17_3613(paaG)
PPSLBJP27_22590
POJPtoMrB4_29630
PPSHG5J76_17050
PVKEPZ47_14265
PEZHWQ56_17510
PBZGN234_04245
PASGKSS96_11835
PALVKSS97_15870
PZAHU749_014410
AVNAvin_14230(ech)
AVLAvCA_14230(ech)
AVDAvCA6_14230(ech)
ACXAchr_28510(ech)
ACBA1S_1111
ABYABAYE2628(hcaA)
ABNAB57_1195
ABBABBFA_02401
ABABBJAB0715_01301
ABAZP795_11770
ABAUIX87_05290
ABAAIX88_07805
ABALABLAC_19520
ACCBDGL_000391(hcaA)
ANORR32_12615
ALCOTEC02_13360
ACALBUM88_05410
ASEII8T81_13390
ACDAOLE_13745
ACIACIAD1726(hcaA)
AEIAOY20_07255
AHLAHTJS_11620
ASOLBEN76_04875
AUGURS_0068
ATNFM020_02780
ALRDS731_16870
CSACsal_0278
HAMHALO0103
HOLHORIV_70970
HSRHSBAA_65020
HMDCTT34_17570
HTTHZS52_05320
GSNYC6258_03918
GBIPG2T_09160 PG2T_14415
SALNSALB1_1097
NBLGJV52_02875
VITADP71_15880
RSORSp0225(fca)
RSLRPSI07_mp0178
RSNRSPO_m00213(fca)
RSMCMR15_mp10197
RSEF504_3664
RSYRSUY_35580
RPUCDC45_18740
REUReut_B4870
BMABMAA0629
BMLBMA10229_0837
BMNBMA10247_A1802
BMALDM55_4800
BMAEDM78_3189
BMAQDM76_3754
BMAIDM57_12400
BMAFDM51_4342
BMAZBM44_4790
BMABBM45_4942
BPSBPSS0779
BPMBURPS1710b_A2361(ech)
BPLBURPS1106A_A1067
BPSEBDL_4061
BPSMBBQ_5363
BPSUBBN_4233
BPSDBBX_5899
BPZBP1026B_II0857
BPQBPC006_II1091
BPSHDR55_4562
BPSABBU_5259
BSAVWS86_22695
BVIBcep1808_3841
BVEAK36_4870
BURBcep18194_B0050
BCNBcen_5223
BCHBcen2424_5636
BCMBcenmc03_4593
BCJBCAM2793
BCENDM39_5052
BCEWDM40_3360
BCEOI35_6672
BAMBamb_4916
BACBamMC406_5465
BMUBmul_3210
BMKDM80_4590
BMULNP80_3343
BCTGEM_5614
BCEDDM42_5195
BCEPAPZ15_24560
BDLAK34_5013
BPYRABD05_21670
BCONNL30_17810
BUBBW23_3981
BDFWI26_26525
BLATWK25_29380
BTEIWS51_10605
BSEMWJ12_33825
BPSLWS57_00300
BMECWJ16_32335
BSTGWT74_32690
BSTLBBJ41_27785
BANNJFN94_17985
BGLbglu_2g10520
BGUKS03_4869 KS03_5262
BUGBC1001_3917
BGFBC1003_5483
BGDbgla_2g02340
BGOBM43_7003
BUKMYA_3497
BULBW21_6349
BUQAC233_21875
BGPBGL_2c16130
BPLAbpln_2g16800
BUDAQ610_19070
BURKDM992_25725
BGEBC1002_5523
BPXBUPH_00501
BPYBphyt_4022
PSPWBJG93_19810
PARBCJU94_22040
PHSC2L64_47315
PTERC2L65_07690
PGPCUJ91_21650
PCJCUJ87_23295
PTSCUJ90_22615
PGISI6I06_26900
PACPFAZ97_28995
PACSFAZ98_16200
PPKU875_18600
PPNODA70_11115
PPNMLV28_19940
PRBX636_15510
PPULRO07_14150
PSPUNA29_22960
PAPISG18_13975
PVEUC34_05415
POXMB84_09805
PFGAB870_16385
PNRAT302_01620
PFIBPI93_022985
BFZBAU07_13705 BAU07_13710
BOHAKI39_13450
CDNBN940_18131
AFQAFA_15960
AAQUD3M96_17090
PHNPAEH1_09180
PIGEGT29_12310 EGT29_21795
DACDaci_2758
DELDelCs14_1643 DelCs14_3999
DTSBI380_09895
DHKBO996_12715
DLAI6G47_10435
DIHG7047_21870
MASWAM586_11545
MALIEYF70_13790
MUMFCL38_05965
MFLAGO485_29925
AVPAVENP_2147
MLOmlr1841
MLNA9174_17315
MHUAMCHK_3418
MJREB229_17555
MERDEB233_14840
ORMHTY61_17840
AVIAvi_1705(fadB)
AGCBSY240_2184
ARUIG6M88_15125
RECRHECIAT_PC0000921(ech)
REPIE4803_PC00561
REIIE4771_PD00572
RLEpRL120505(ech)
RLTRleg2_4901
RLGRleg_4811
RLBRLEG3_07850
RLURLEG12_10850
RHLLPU83_1914
RPHAAMC79_PD00928
RADCO657_27460
RIIFFM53_027655
RHIDFFM81_024610
RBQJ2J99_23600
RLNJ0663_14160
RRGJ3P73_26520
RLSHB780_12705
NGLRG1141_PA00800 RG1141_PA00830
NGGRG540_PA00850 RG540_PA00880
BAPIBBC0122_015010
METM446_3478
METAY590_19210
RHZRHPLAN_21410 RHPLAN_24560 RHPLAN_30660 RHPLAN_30710 RHPLAN_37820
PSINCAK95_07155
PSTGE8M01_25970
CCRCC_2401
CCSCCNA_02484
CAKCaul_1132
CSECseg_2345 Cseg_3073
CAULKCG34_00040
BSBBresu_2425
BRFE4M01_02205
PYEA6J80_19600
NARSaro_1669
NPPPP1Y_AT13185 PP1Y_Mpl6773
NPNJI59_05910
NOTC7W88_11060
NORFA702_13690
NDRHT578_02620 HT578_07725
SPHITS85_18585
SSANNX02_02990
SPANAWL63_04670
SKRBRX40_12255
SPHCCVN68_17210
SPIIG7077_01560
SSUAFPZ54_06255 FPZ54_18010
SJPSJA_C1-02370(menB)
SCHSphch_3903
SSYSLG_07870(ferB2) SLG_25030(ferB)
SPHRBSY17_3548
SHYDCJD35_16325
SPYGYGS_C2P0044 YGS_C2P1453
SAMISAMIE_1030330
SPHGAZE99_04770
SFLASPHFLASMR4Y_00329
SPHYCHN51_00865
BLASBSY18_3470
BFWB5J99_08145
SPHSETR14_08000
POQKZX46_07310
ALBAEB_P1354
AAYWYH_03221
CMANA9D14_16035
ERYCP97_14605
RGIRGI145_19910
ROSCTJ15_00100
RMUCFOB66_02760
SHUMSTHU_10230
SVCSTVA_44450
AZLAZL_b03680(paaG)
AZZDEW08_27025
NAOY958_22070 Y958_28945 Y958_29935
NCBC0V82_17725
RPMRSPPHO_02617
PARHI5S86_11630 I5S86_14465
NTPCRH09_15840
NYALTV02_37285
REBXU06_30340
ACTWF7P10_10885
AGRAAGRA3207_004415
SENSACE_2794
SVISvir_26730
AMQAMETH_4411
AABA4R43_08645
AMYYYIM_23925
PSEEFRP1_10310
PSEQAD006_17860
PECQAD017_25695
PHHAFB00_24520
PAUTPdca_42230
APRECNX65_20610
AMIAmir_4116
SSYIEKG83_28030
KALKALB_2035
AEYCDG81_03320
SUSAcid_0255
SMIZ4412673_04091(menB)
SPHZE3D81_00020
 » 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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