KEGG   ENZYME: 4.1.99.24
Entry
EC 4.1.99.24                Enzyme                                 
Name
L-tyrosine isonitrile synthase;
pvcA (gene name)
Class
Lyases;
Carbon-carbon lyases;
Other carbon-carbon lyases
Sysname
L-tyrosine:D-ribulose-5-phosphate lyase (isonitrile-forming)
Reaction(IUBMB)
L-tyrosine + D-ribulose 5-phosphate = (2S)-3-(4-hydroxyphenyl)-2-isocyanopropanoate + hydroxyacetone + formaldehyde + phosphate + H2O [RN:R12150]
Reaction(KEGG)
R12150
Substrate
L-tyrosine [CPD:C00082];
D-ribulose 5-phosphate [CPD:C00199]
Product
(2S)-3-(4-hydroxyphenyl)-2-isocyanopropanoate [CPD:C21889];
hydroxyacetone [CPD:C05235];
formaldehyde [CPD:C00067];
phosphate [CPD:C00009];
H2O [CPD:C00001]
Comment
The enzymes from the bacteria Pseudomonas aeruginosa and Xenorhabdus nematophila are involved in the biosynthesis of paerucumarin and rhabduscin, respectively. According to the proposed mechanism, the enzyme forms an imine intermediate composed of linked L-tyrosine and D-ribulose 5-phosphate, followed by loss of the phosphate group and formation of a beta-keto imine and keto-enol tautomerization. This is followed by a C-C bond cleavage, the release of hydroxyacetone, and a retro aldol type reaction that releases formaldehyde and forms the final product [3]. cf. EC 4.1.99.25, L-tryptophan isonitrile synthase.
History
EC 4.1.99.24 created 2018
Pathway
ec00997  Biosynthesis of various other secondary metabolites
Orthology
K22952  L-tyrosine isonitrile synthase
Genes
SMAR: SM39_0023(pvcA)
SMAC: SMDB11_0021(pvcA)
SMW: SMWW4_v1c06950
SPE: Spro_0703
SRR: SerAS9_0643
SRL: SOD_c05750(pvcA)
SRY: M621_03035
SPLY: Q5A_003035
SRS: SerAS12_0643
SRA: SerAS13_0643
SLQ: M495_02875
SERF: L085_00785
SERS: SERRSCBI_03165
SQU: E4343_13100
SFJ: SAMEA4384070_0731
SSUR: ATE40_000105
SURI: J0X03_20650
SENP: KHA73_03080
SNEM: NLX84_03215
SNEV: OI978_03210
SGRI: SGBXF1_00642
SSAR: SSARUM_000637
FSM: CCS41_08780
ECA: ECA3381(pvcA)
PATR: EV46_16845
PATO: GZ59_34180(pvcA)
PCT: PC1_3225
PCC: PCC21_032130
PCV: BCS7_16170
PWA: Pecwa_1103
PPAR: A8F97_13430
PEC: W5S_0995
PWS: A7983_12890
PPOA: BJK05_11150
PBRA: B5S52_05625
PPUJ: E2566_16440
PARI: I2D83_05685
PAQU: DMB82_0005330
PVZ: OA04_34840(pvcA)
PPAV: LOZ86_16800
PQU: IG609_004780
PPOO: LW347_16215
PCAC: OI450_12745
PACB: M9782_18495
PARL: PEC302110_29790(pvcA)
PPEU: DUT67_05215(pvcA)
DDD: Dda3937_01910
DZE: Dd1591_3133
DSO: A4U42_14185
DFN: CVE23_05630
DDQ: DDI_0820
EAM: EAMY_1788(pvcA)
EAY: EAM_1751(pvcA)
ERJ: EJP617_29230(pvcA)
PLU: plu2816
PLUM: A4R40_14040
PAY: PAU_01721(pvcA)
PTT: VY86_17225
PAKH: B0X70_14355
PLUI: CE143_14350
XBO: XBJ1_1355
XBV: XBW1_1621
XNE: XNC1_1221
XNM: XNC2_1197(isnA)
XDO: XDD1_2893
XPO: XPG1_0843
XHO: A9255_00170
XBU: HGO23_05580 HGO23_15000
XGR: QL128_05125
PMAG: JI723_04265
LEZ: GLE_4813
LYA: RDV84_09225
VAN: VAA_02645
LAG: N175_02895
VAU: VANGNB10_cI2371c(pvcA)
VQI: CCZ37_11630
PAE: PA2254(pvcA)
PAEV: N297_2327
PAEI: N296_2327
PAU: PA14_35430(pvcA)
PAG: PLES_30501(pvcA)
PAF: PAM18_2786(pvcA)
PNC: NCGM2_3264(pvcA)
PAEB: NCGM1900_4276(pvcA)
PDK: PADK2_14005
PSG: G655_13770
PRP: M062_11790
PAEP: PA1S_14350
PAER: PA1R_gp0055
PAEM: U769_13935
PAEL: T223_15580
PAES: SCV20265_3072
PAEU: BN889_02459(pvcA_1)
PAEG: AI22_19505
PAEC: M802_2324
PAEO: M801_2326
SECH: B18_23345
PAP: PSPA7_2987(pvcA)
PPAA: B7D75_13690
PMOS: O165_028275
PCG: AXG94_21615
PMED: E3Z27_06015
PEN: PSEEN0962
PLQ: AA042_05060
PSEC: CCOS191_4460
PDW: BV82_0208
PTRT: HU722_0010630
PMUY: KSS95_23395
PORY: EJA05_23555
PTK: EXN22_05845
PSIH: LOY51_22400
PCUC: PSH97_11750
ACD: AOLE_01050
SPSH: FM037_15205
THAT: H3N35_24275
TACT: SG35_025290
TVD: SG34_003210
PPIS: B1L02_15135
PSEN: PNC201_02365
ALG: AQULUS_02960
ASIP: AQUSIP_24830
LPN: lpg0174(pvcA)
LPH: LPV_0257
LPO: LPO_0205
LPU: LPE509_03056
LPM: LP6_0178(pvcA)
LPF: lpl0236
LPP: lpp0236
LPC: LPC_0256(pvcA)
LPA: lpa_00341
LPE: lp12_0176
LLO: LLO_2212 LLO_2224
LOK: Loa_01333
LSH: CAB17_16385 CAB17_16450
LLG: 44548918_00376
LIB: E4T55_11455
LCJ: NCTC11976_00382
LSS: NCTC12082_02498
LLY: J2N86_00530
THIP: N838_14010
TOL: TOL_3184
TOR: R615_14970
AHA: AHA_3282
AHY: AHML_17550
AHD: AI20_02945
AHR: V428_18205
AHP: V429_18240
AHJ: V469_05055
AHH: RY45_16930
AHI: VU14_05260
AAJ: BOQ57_16805
ASA: ASA_1024(pvcA)
AEO: O23A_p0207
ADH: CK627_09300
AEJ: E5E97_22355
ABES: IU367_04950
CRZ: D1345_08635
CHAE: CH06BL_18140(pvcA)
IFL: C1H71_18935
BMA: BMAA1924(pvcA)
BMV: BMASAVP1_0939(pvcA)
BML: BMA10229_1224(pvcA)
BMN: BMA10247_A2201(pvcA)
BMAZ: BM44_3822
BMAL: DM55_3863
BMAE: DM78_4782
BMAQ: DM76_4560
BMAI: DM57_06425
BMAF: DM51_3612(pvcA)
BMAB: BM45_4599(pvcA)
BPS: BPSS0160
BPM: BURPS1710b_A1679(pvcA)
BPL: BURPS1106A_A0228(pvcA)
BPD: BURPS668_A0318(pvcA)
BPSE: BDL_6051
BPSM: BBQ_6054
BPSU: BBN_3540
BPSD: BBX_5221
BPZ: BP1026B_II0180
BPQ: BPC006_II0217
BPK: BBK_5352
BPSH: DR55_5202
BPSA: BBU_3412
BPSO: X996_4970
BUT: X994_4519(pvcA)
BTE: BTH_II0229
BTQ: BTQ_3524
BTJ: BTJ_4561
BTZ: BTL_5348
BTV: BTHA_4853
BTHE: BTN_5019
BTHM: BTRA_5287
BTHA: DR62_5149
BTHL: BG87_5354(pvcA)
BOK: DM82_3791
BOC: BG90_4252(pvcA)
BUU: WS70_27865
BSAV: WS86_29770
BUB: BW23_5844(pvcA)
BSTG: WT74_18885 WT74_28470
PBRY: NDK50_11480
AGT: EYD00_23500
MAQU: Maq22A_c27625
MEE: DA075_00550
MTEA: DK419_10180
MIND: mvi_13000
MLD: U0023_25345 U0023_25355
FIL: BN1229_v1_2105
FIY: BN1229_v1_2105
PACE: A6070_11560
SUR: STAUR_0256(pvcA)
AGE: AA314_03098 AA314_05405
BBA: Bd1454(pvcA)
BBAT: Bdt_1440(pvcA)
BBAC: EP01_03530
BDQ: CIK05_01005
BSTO: C0V70_01910
PSTI: SOO65_09690
PIJ: QEJ31_03455 QEJ31_14485
UAM: UABAM_00791 UABAM_02081
CHF: KTO58_07940
CHIM: CK934_21075
HSW: Hsw_PA0221
FSD: LXD69_13605
AQR: HN014_13190
BTRO: FJR70_30880
LGE: C269_01330
ESS: ATZ33_00390
MSTO: MSTO_36450(pvcA)
CCYS: SAMEA4530656_2636
CLIZ: G7Y31_00815
CQN: G7Y29_02320
NBR: O3I_007385
NIE: KV110_36475
NGP: LTT66_00585
NSPU: IFM12276_39660(pvcA)
TPR: Tpau_3777
SGRF: SGFS_103430
SRC: M271_02550
SALS: SLNWT_6358
STRE: GZL_02117 GZL_07546
SLD: T261_7381
SLC: SL103_14585
SRW: TUE45_01198
SRN: A4G23_02272 A4G23_02288
SGS: AVL59_26190
SGM: GCM10017557_01810(pvcA)
SCAD: DN051_13680 DN051_33290
SNR: SNOUR_09495 SNOUR_35375 SNOUR_38585
SALU: DC74_1046
SALL: SAZ_05705
SPUN: BFF78_37575
SGV: B1H19_07080
SALJ: SMD11_5635
STRO: STRMOE7_05240
SLK: SLUN_21725
SCYA: EJ357_05730
STIR: DDW44_25450
SRK: FGW37_05190 FGW37_29465
SSPO: DDQ41_27040
SVR: CP971_06750 CP971_07870
SBY: H7H31_12650
SRIM: CP984_10745 CP984_28330
SCHA: CP983_37935
SBAT: G4Z16_03985
SPLA: CP981_03705
SCYG: S1361_05150
SFEU: IM697_17530
SDW: K7C20_00380
SAUH: SU9_002815
SFB: CP974_12510 CP974_12590
SMOB: J7W19_04485 J7W19_31700
SANU: K7396_31920
SINE: KI385_06090
SAOV: G3H79_37810
SNIG: HEK616_25240(pvcA)
STUD: STRTU_006553
SANT: QR300_36525
SYUN: MOV08_09385 MOV08_34970
SOV: QZH56_30865
SCHG: NRO40_12665 NRO40_12745
SINN: ABB07_17555
STRZ: OYE22_12420
STPB: QR97_12255
SRPA: HEP86_05210
SCHE: QRN89_30490
KAU: B6264_01935 B6264_03065
KIT: CFP65_3111
KCH: O1G21_10630
RSA: RSal33209_2067(pvcA)
FRA: Francci3_2754
AAB: A4R43_21580
AMYY: YIM_23650
PSEH: XF36_24020
PHH: AFB00_21845 AFB00_29825
KAL: KALB_6297
ALO: CRK57529
PMAD: BAY61_18530
CROS: N8J89_22515 N8J89_32275
MSAG: GCM10017556_09890(pvcA)
 » show all
Reference
1  [PMID:18689486]
  Authors
Clarke-Pearson MF, Brady SF
  Title
Paerucumarin, a new metabolite produced by the pvc gene cluster from Pseudomonas  aeruginosa.
  Journal
J Bacteriol 190:6927-30 (2008)
DOI:10.1128/JB.00801-08
Reference
2  [PMID:18824174]
  Authors
Drake EJ, Gulick AM
  Title
Three-dimensional structures of Pseudomonas aeruginosa PvcA and PvcB, two proteins involved in the synthesis of 2-isocyano-6,7-dihydroxycoumarin.
  Journal
J Mol Biol 384:193-205 (2008)
DOI:10.1016/j.jmb.2008.09.027
  Sequence
[pae:PA2254]
Reference
3  [PMID:28212039]
  Authors
Chang WC, Sanyal D, Huang JL, Ittiamornkul K, Zhu Q, Liu X
  Title
In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate.
  Journal
Org Lett 19:1208-1211 (2017)
DOI:10.1021/acs.orglett.7b00258
Other DBs
ExplorEnz - The Enzyme Database: 4.1.99.24
IUBMB Enzyme Nomenclature: 4.1.99.24
ExPASy - ENZYME nomenclature database: 4.1.99.24
BRENDA, the Enzyme Database: 4.1.99.24
LinkDB

DBGET integrated database retrieval system