KEGG   ENZYME: 3.11.1.1Help
Entry
EC 3.11.1.1                 Enzyme                                 

Name
phosphonoacetaldehyde hydrolase;
phosphonatase;
2-phosphonoacetylaldehyde phosphonohydrolase
Class
Hydrolases;
Acting on carbon-phosphorus bonds;
Acting on carbon-phosphorus bonds (only sub-subclass identified to date)
BRITE hierarchy
Sysname
2-oxoethylphosphonate phosphonohydrolase
Reaction(IUBMB)
phosphonoacetaldehyde + H2O = acetaldehyde + phosphate [RN:R00747]
Reaction(KEGG)
Substrate
phosphonoacetaldehyde [CPD:C03167];
H2O [CPD:C00001]
Product
acetaldehyde [CPD:C00084];
phosphate [CPD:C00009]
Comment
This enzyme destabilizes the C-P bond, by forming an imine between one of its lysine residues and the carbonyl group of the substrate, thus allowing this, normally stable, bond to be broken. The mechanism is similar to that used by EC 4.1.2.13, fructose-bisphosphate aldolase, to break a C-C bond. Belongs to the haloacetate dehalogenase family.
History
EC 3.11.1.1 created 1972, modified 1976, modified 2001
Pathway
ec00440  Phosphonate and phosphinate metabolism
ec01100  Metabolic pathways
ec01120  Microbial metabolism in diverse environments
Orthology
K05306  phosphonoacetaldehyde hydrolase
Genes
STY: STY0471(phnX)
STT: t2431(phnX)
SEX: STBHUCCB_25710
SENT: TY21A_12335
STM: STM0432(phnX)
SEO: STM14_0511(phnX)
SEV: STMMW_05021
SEY: SL1344_0426(phnX)
SEM: STMDT12_C04960
SEJ: STMUK_0438(phnX)
SEB: STM474_0452(phnX)
SEF: UMN798_0475(phnX)
SENR: STMDT2_04281(phnX)
SEND: DT104_04771(phnX)
SENI: CY43_02500
SPT: SPA2291(phnX)
SEK: SSPA2133
SEI: SPC_0444(phnX)
SEC: SCH_0473(phnX)
SEH: SeHA_C0534(phnX)
SHB: SU5_01124
SEE: SNSL254_A0479(phnX)
SEW: SeSA_A0492(phnX)
SEA: SeAg_B0471(phnX)
SENS: Q786_02125
SED: SeD_A0473
SEG: SG0443(phnX)
SEL: SPUL_2535(phnX)
SEGA: SPUCDC_2521(phnX)
SET: SEN0414(phnX)
SENA: AU38_02115
SENO: AU37_02110
SENV: AU39_02115
SENQ: AU40_02345
SENL: IY59_02165
SEEP: I137_11540
SENB: BN855_4290(phnX)
SENE: IA1_02310
KPN: KPN_04064(phnX)
KPU: KP1_5437(phnX)
KPP: A79E_0043
KPT: VK055_3400(phnX)
KPR: KPR_0042(phnX)
KPJ: N559_0076
KPX: PMK1_01570(phnX)
KPNU: LI86_00215
KPNK: BN49_0043(phnX)
KOX: KOX_06380
KOE: A225_5750
EAE: EAE_06840
EAR: CCG32638
SMAR: SM39_1582(phnX)
SMAC: SMDB11_1394(phnX)
SMW: SMWW4_v1c21480(phnX)
SMAF: D781_1948
SERF: L085_18015
SFJ: SAMEA4384070_2178(phnX)
PMR: PMI3079(phnX)
PMIB: BB2000_3090(phnX)
PRG: RB151_040690(phnX)
PHEI: NCTC12003_03584(phnX)
ETE: ETEE_2729(phnX)
VCH: VCA0606
VCS: MS6_A0655
VCE: Vch1786_II0291(phnX)
VCI: O3Y_16378
VCO: VC0395_0548(phnX)
VCR: VC395_A0709(phnX)
VCM: VCM66_A0564(phnX)
VCX: VAA049_2332(phnX)
VCZ: VAB027_558(phnX)
VVU: VV2_1662(phnX)
VVY: VVA0474
VPA: VPA0233
VAG: N646_3667
VSP: VS_II0396
VTA: B0684(phnX)
PAE: PA1311(phnX)
PAEV: N297_1351(phnX)
PAEI: N296_1351(phnX)
PAU: PA14_47280(phnX)
PAP: PSPA7_4080(phnX)
PAG: PLES_38711(phnX)
PAF: PAM18_3592(phnX)
PNC: NCGM2_2197(phnX)
PAEB: NCGM1900_5262(phnX)
PAEP: PA1S_19350
PAEM: U769_19195
PAEL: T223_19800
PAEU: BN889_01413(phnX)
PAEG: AI22_15250
PAEC: M802_1348(phnX)
PAEO: M801_1350(phnX)
PRE: PCA10_07740(phnX) PCA10_23870(phnX)
PCQ: PcP3B5_33840(phnX_2)
PPU: PP_2208(phnX)
PPF: Pput_3530
PPT: PPS_1819
PPI: YSA_01369
PPX: T1E_0555(phnX)
PPUH: B479_08985
PPUT: L483_08840
PPUN: PP4_32670(phnX) PP4_36070(phnX)
PPUD: DW66_2067
PMON: X969_06930
PMOT: X970_06905
PFL: PFL_3966(phnX)
PPRC: PFLCHA0_c40250(phnX)
PPRO: PPC_4065
PFS: PFLU_3912
PFC: PflA506_3287(phnX)
PFB: VO64_0990
PMAN: OU5_0003 OU5_1265(phnX)
PFW: PF1751_v1c33500(phnX)
PEN: PSEEN3554(phnX)
PPUU: PputUW4_01745(phnX1) PputUW4_02573(phnX2)
PKC: PKB_3136(phnX)
PSEM: TO66_20550
PSEC: CCOS191_1692(phnX)
PSOS: POS17_4075
PANR: A7J50_3573
PSET: THL1_824
ACB: A1S_1365
ABY: ABAYE2317(phnX)
ABN: AB57_1573
ABB: ABBFA_02116(phnX)
ABX: ABK1_1828
ABH: M3Q_1739
ABAZ: P795_10490
ABAU: IX87_03565
ABAA: IX88_08675
ACC: BDGL_000723(phnX)
AGU: AS4_30470(phnX)
SPSW: Sps_04132
PSEO: OM33_17385
PSPO: PSPO_b1177(phnX)
PSEN: PNC201_02520(phnX)
MHC: MARHY1154(phnX)
MBS: MRBBS_3416(phnX)
MARJ: MARI_09750(phnX)
PIN: Ping_2749
MVS: MVIS_0355(phnX)
MYA: MORIYA_2609(phnX)
ASIP: AQUSIP_09810(phnX)
HCH: HCH_03084(phnX)
HAM: HALO0564
HBE: BEI_2637(phnX)
OAI: OLEAN_C33610(phnX)
AHA: AHA_1940(phnX)
AVR: B565_1687
ACAV: VI35_09530
AEL: NCTC12917_03269(phnX)
OCE: GU3_01360
RPI: Rpic_4474
RIN: ACS15_4485(phnX)
BCEN: DM39_4565(phnX)
BPSL: WS57_10885
BGU: KS03_3971(phnX)
BGO: BM43_6455(phnX)
BXE: Bxe_A2117
BXB: DR64_4272(phnX)
BPE: BP2275
BPC: BPTD_2235
BPER: BN118_0793
BPET: B1917_2184
BPEU: Q425_16350
BPA: BPP2453
BBR: BB1901
BAV: BAV1192(phnX)
BHO: D560_2397
BHM: D558_2383
BHZ: ACR54_03229(phnX)
BTRM: SAMEA390648702668(phnX)
AXY: AXYL_01820(phnX)
AXX: ERS451415_01702(phnX)
DAC: Daci_2412
CTES: O987_20200
LIH: L63ED372_02133(phnX)
HSE: Hsero_2624(phnX)
HRB: Hrubri_2707(phnX)
SUTT: SUTMEG_18320(phnX)
RGE: RGE_31440(phnX)
SMUL: SMUL_2959
DVM: DvMF_0514
DGG: DGI_0772
DWD: DSCW_57730(phnX)
SNO: Snov_4455
HDI: HDIA_3284(phnX)
CAK: Caul_2989
CSE: Cseg_3206
RCP: RCAP_rcc03375(phnX)
OAR: OA238_c39220(phnX)
RHC: RGUI_0659
LABT: FIU93_18155(phnX)
ROH: FIU89_05565(phnX)
SPHK: SKP52_20485(phnX)
SPHP: LH20_01285
SSY: SLG_17040(phnX)
ALB: AEB_P1097
GXL: H845_1626
AZL: AZL_a10480(phnX)
ALI: AZOLI_p20204(phnX)
PGV: SL003B_3090(phnX)
BAN: BA_1340(phnX)
BAR: GBAA_1340(phnX)
BAT: BAS1239
BAH: BAMEG_3256(phnX)
BAI: BAA_1407(phnX)
BANT: A16_13840
BANR: A16R_14030
BANS: BAPAT_1258
BANV: DJ46_165(phnX)
BCE: BC1326
BCA: BCE_1439(phnX)
BCZ: BCE33L1217(phnX)
BCR: BCAH187_A1480(phnX)
BCB: BCB4264_A1377(phnX)
BCU: BCAH820_1414(phnX)
BCG: BCG9842_B3967(phnX)
BCQ: BCQ_1398(phnX)
BCX: BCA_1378(phnX)
BAL: BACI_c13600(phnX)
BNC: BCN_1299
BCF: bcf_06710
BCER: BCK_01760
BTK: BT9727_1215(phnX)
BTL: BALH_1189
BTB: BMB171_C1169(phnX)
BTT: HD73_1555
BTHI: BTK_07920
BTC: CT43_CH1256(phnX)
BTM: MC28_0554(phnX)
BTG: BTB_c13690(phnX)
BTI: BTG_14115
BTW: BF38_2545(phnX)
BWW: bwei_3683(phnX)
BMYO: BG05_4573(phnX)
BMQ: BMQ_3213(phnX)
BMD: BMD_3231(phnX)
BEO: BEH_01675
LSP: Bsph_1361(phnX)
HHD: HBHAL_4064(phnX)
SCA: SCA_0879
BBE: BBR47_44980(phnX)
PPY: PPE_00475
PPM: PPSC2_02690(phnX)
PPO: PPM_0474(phnX)
PPOL: X809_02160
PPOY: RE92_09240
PMW: B2K_03965
KUR: ASO14_1514(phnX)
LPL: lp_0711(phnX)
LPJ: JDM1_0587(phnX)
LPT: zj316_0779(phnX)
LPS: LPST_C0542(phnX)
LPZ: Lp16_0561
LSA: LCA_1665(phnX)
EFM: M7W_1184
EMU: EMQU_1817
CBV: U729_679(phnX)
BPRO: PMF13cell1_01419(phnX)
CSO: CLS_31070
EHL: EHLA_0403
CDF: CD630_28490(phnXW)
PDC: CDIF630_03116(phnXW)
PDF: CD630DERM_28490(phnXW)
ELM: ELI_2329
PFT: JBW_03190
TBW: NCTC13354_01320(phnX)
BSCA: BBSC_0729
ELE: Elen_2313
RCA: Rcas_0966
CAP: CLDAP_13860(phnX)
AGL: PYTT_0871
PSL: Psta_2132
MFF: MFFC18_39430(phnX)
PLM: Plim_3627
PEH: Spb1_01260(phnX)
PLS: VT03_23990(phnX)
FMR: Fuma_02296(phnX)
GMR: GmarT_01730(phnX)
BVO: Pan97_26590(phnX_1) Pan97_29700(phnX_2)
GES: VT84_36540(phnX)
GOG: C1280_29860(phnX)
IPA: Isop_0931
SACI: Sinac_0397
AGV: OJF2_20220(phnX)
FVA: FV113G1_24050(phnX)
BFR: BF3696
BVU: BVU_3007
BOA: Bovatus_01971(phnX)
BCEL: BcellWH2_05390(phnX)
BCAC: CGC64_17840(phnX)
BUN: Bun01g_35860(phnX)
PDI: BDI_2852
 » show all
Taxonomy
Reference
1  [PMID:4982500]
  Authors
La Nauze JM, Rosenberg H.
  Title
The identification of 2-phosphonoacetaldehyde as an intermediate in the degradation of 2-aminoethylphosphonate by Bacillus cereus.
  Journal
Biochim Biophys Acta 165:438-47 (1968)
DOI:10.1016/0304-4165(68)90223-7
Reference
2  [PMID:4989158]
  Authors
La Nauze JM, Rosenberg H, Shaw DC.
  Title
The enzymic cleavage of the carbon-phosphorus bond: purification and properties of phosphonatase.
  Journal
Biochim Biophys Acta 212:332-50 (1970)
DOI:10.1016/0005-2744(70)90214-7
Reference
3  [PMID:200222]
  Authors
La Nauze JM, Coggins JR, Dixon HB.
  Title
Aldolase-like imine formation in the mechanism of action of phosphonoacetaldehyde hydrolase.
  Journal
Biochem J 165:409-11 (1977)
DOI:10.1042/bj1650409
Reference
4  [PMID:3132206]
  Authors
Olsen DB, Hepburn TW, Moos M, Mariano PS, Dunaway-Mariano D.
  Title
Investigation of the Bacillus cereus phosphonoacetaldehyde hydrolase. Evidence for a Schiff base mechanism and sequence analysis of an active-site peptide containing the catalytic lysine residue.
  Journal
Biochemistry 27:2229-34 (1988)
DOI:10.1021/bi00406a063
Reference
5  [PMID:9649311]
  Authors
Baker AS, Ciocci MJ, Metcalf WW, Kim J, Babbitt PC, Wanner BL, Martin BM, Dunaway-Mariano D.
  Title
Insights into the mechanism of catalysis by the P-C bond-cleaving enzyme phosphonoacetaldehyde hydrolase derived from gene sequence analysis and mutagenesis.
  Journal
Biochemistry 37:9305-15 (1998)
DOI:10.1021/bi972677d
  Sequence
[stm:STM0432]
Other DBs
ExplorEnz - The Enzyme Database: 3.11.1.1
IUBMB Enzyme Nomenclature: 3.11.1.1
ExPASy - ENZYME nomenclature database: 3.11.1.1
BRENDA, the Enzyme Database: 3.11.1.1
CAS: 37289-42-2

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