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
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
SERF: L085_00785
ECA: ECA3381(pvcA)
PATR: EV46_16845
PATO: GZ59_34180(pvcA)
PCT: PC1_3225
PEC: W5S_0995
DDQ: DDI_0820
EAM: EAMY_1788(pvcA)
EAY: EAM_1751(pvcA)
ERJ: EJP617_29230(pvcA)
PLU: plu2816
PAY: PAU_01721(pvcA)
XBO: XBJ1_1355
XBV: XBW1_1621
XNE: XNC1_1221
XNM: XNC2_1197(isnA)
XDO: XDD1_2893
XPO: XPG1_0843
LEZ: GLE_4813
VAN: VAA_02645
VAU: VANGNB10_cI2371c(pvcA)
PAE: PA2254(pvcA)
PAEV: N297_2327
PAEI: N296_2327
PAU: PA14_35430(pvcA)
PAP: PSPA7_2987(pvcA)
PAG: PLES_30501(pvcA)
PAF: PAM18_2786(pvcA)
PNC: NCGM2_3264(pvcA)
PAEB: NCGM1900_4276(pvcA)
PAEP: PA1S_14350
PAEM: U769_13935
PAEL: T223_15580
PAEU: BN889_02459(pvcA_1)
PAEG: AI22_19505
PAEC: M802_2324
PAEO: M801_2326
PEN: PSEEN0962
LPN: lpg0174(pvcA)
LPH: LPV_0257
LPO: LPO_0205
LPM: LP6_0178(pvcA)
LPF: lpl0236
LPP: lpp0236
LPC: LPC_0256(pvcA)
LPA: lpa_00341
LPE: lp12_0176
LOK: Loa_01333
TOL: TOL_3184
AHA: AHA_3282
ASA: ASA_1024(pvcA)
CHAE: CH06BL_18140(pvcA)
BMA: BMAA1924(pvcA)
BMV: BMASAVP1_0939(pvcA)
BML: BMA10229_1224(pvcA)
BMN: BMA10247_A2201(pvcA)
BMAL: DM55_3863
BMAE: DM78_4782
BMAQ: DM76_4560
BMAI: DM57_06425
BMAF: DM51_3612(pvcA)
BMAZ: BM44_3822
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
BPK: BBK_5352
BPSH: DR55_5202
BPSA: BBU_3412
BPSO: X996_4970
BUT: X994_4519(pvcA)
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)
BUB: BW23_5844(pvcA)
SUR: STAUR_0256(pvcA)
SECH: B18_23345
BBA: Bd1454(pvcA)
BBAT: Bdt_1440(pvcA)
BBAC: EP01_03530
TPR: Tpau_3777
SALS: SLNWT_6358
SALU: DC74_1046
SALL: SAZ_05705
SLD: T261_7381
SALJ: SMD11_5635
RSA: RSal33209_2067(pvcA)
AMYY: YIM_23650
PSEH: XF36_24020
KAL: KALB_6297
ALO: CRK57529
 » 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