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
SMARSM39_0023(pvcA)
SMACSMDB11_0021(pvcA)
SMWSMWW4_v1c06950
SPESpro_0703
SRRSerAS9_0643
SRLSOD_c05750(pvcA)
SRYM621_03035
SPLYQ5A_003035
SRSSerAS12_0643
SRASerAS13_0643
SLQM495_02875
SERFL085_00785
SERSSERRSCBI_03165
SQUE4343_13100
SFJSAMEA4384070_0731
SSURATE40_000105
SURIJ0X03_20650
SENPKHA73_03080
SNEMNLX84_03215
SNEVOI978_03210
FSMCCS41_08780
ECAECA3381(pvcA)
PATREV46_16845
PATOGZ59_34180(pvcA)
PCTPC1_3225
PCCPCC21_032130
PCVBCS7_16170
PWAPecwa_1103
PPARA8F97_13430
PECW5S_0995
PWSA7983_12890
PPOABJK05_11150
PBRAB5S52_05625
PPUJE2566_16440
PARII2D83_05685
PAQUDMB82_0005330
PVZOA04_34840(pvcA)
PPAVLOZ86_16800
PQUIG609_004780
PPOOLW347_16215
PCACOI450_12745
PACBM9782_18495
DDDDda3937_01910
DZEDd1591_3133
DSOA4U42_14185
DFNCVE23_05630
DDQDDI_0820
EAMEAMY_1788(pvcA)
EAYEAM_1751(pvcA)
ERJEJP617_29230(pvcA)
PLUplu2816
PLUMA4R40_14040
PAYPAU_01721(pvcA)
PTTVY86_17225
PAKHB0X70_14355
PLUICE143_14350
XBOXBJ1_1355
XBVXBW1_1621
XNEXNC1_1221
XNMXNC2_1197(isnA)
XDOXDD1_2893
XPOXPG1_0843
XHOA9255_00170
XBUHGO23_05580 HGO23_15000
XGRQL128_05125
PMAGJI723_04265
LEZGLE_4813
LYARDV84_09225
VANVAA_02645
LAGN175_02895
VAUVANGNB10_cI2371c(pvcA)
VQICCZ37_11630
PAEPA2254(pvcA)
PAEVN297_2327
PAEIN296_2327
PAUPA14_35430(pvcA)
PAPPSPA7_2987(pvcA)
PAGPLES_30501(pvcA)
PAFPAM18_2786(pvcA)
PNCNCGM2_3264(pvcA)
PAEBNCGM1900_4276(pvcA)
PDKPADK2_14005
PSGG655_13770
PRPM062_11790
PAEPPA1S_14350
PAERPA1R_gp0055
PAEMU769_13935
PAELT223_15580
PAESSCV20265_3072
PAEUBN889_02459(pvcA_1)
PAEGAI22_19505
PAECM802_2324
PAEOM801_2326
PPAAB7D75_13690
PMOSO165_028275
PCGAXG94_21615
PMEDE3Z27_06015
PENPSEEN0962
PLQAA042_05060
PSECCCOS191_4460
PDWBV82_0208
PTRTHU722_0010630
PMUYKSS95_23395
PORYEJA05_23555
PTKEXN22_05845
PSIHLOY51_22400
PCUCPSH97_11750
ACDAOLE_01050
SPSHFM037_15205
THATH3N35_24275
TACTSG35_025290
TVDSG34_003210
PPISB1L02_15135
PSENPNC201_02365
ALGAQULUS_02960
ASIPAQUSIP_24830
LPNlpg0174(pvcA)
LPHLPV_0257
LPOLPO_0205
LPULPE509_03056
LPMLP6_0178(pvcA)
LPFlpl0236
LPPlpp0236
LPCLPC_0256(pvcA)
LPAlpa_00341
LPElp12_0176
LLOLLO_2212 LLO_2224
LOKLoa_01333
LSHCAB17_16385 CAB17_16450
LLG44548918_00376
LIBE4T55_11455
LCJNCTC11976_00382
LSSNCTC12082_02498
LLYJ2N86_00530
THIPN838_14010
TOLTOL_3184
TORR615_14970
AHAAHA_3282
AHYAHML_17550
AHDAI20_02945
AHRV428_18205
AHPV429_18240
AHJV469_05055
AHHRY45_16930
AHIVU14_05260
AAJBOQ57_16805
ASAASA_1024(pvcA)
AEOO23A_p0207
ADHCK627_09300
AEJE5E97_22355
ABESIU367_04950
CRZD1345_08635
CHAECH06BL_18140(pvcA)
IFLC1H71_18935
BMABMAA1924(pvcA)
BMVBMASAVP1_0939(pvcA)
BMLBMA10229_1224(pvcA)
BMNBMA10247_A2201(pvcA)
BMALDM55_3863
BMAEDM78_4782
BMAQDM76_4560
BMAIDM57_06425
BMAFDM51_3612(pvcA)
BMAZBM44_3822
BMABBM45_4599(pvcA)
BPSBPSS0160
BPMBURPS1710b_A1679(pvcA)
BPLBURPS1106A_A0228(pvcA)
BPDBURPS668_A0318(pvcA)
BPSEBDL_6051
BPSMBBQ_6054
BPSUBBN_3540
BPSDBBX_5221
BPZBP1026B_II0180
BPQBPC006_II0217
BPKBBK_5352
BPSHDR55_5202
BPSABBU_3412
BPSOX996_4970
BUTX994_4519(pvcA)
BTEBTH_II0229
BTQBTQ_3524
BTJBTJ_4561
BTZBTL_5348
BTVBTHA_4853
BTHEBTN_5019
BTHMBTRA_5287
BTHADR62_5149
BTHLBG87_5354(pvcA)
BOKDM82_3791
BOCBG90_4252(pvcA)
BUUWS70_27865
BSAVWS86_29770
BUBBW23_5844(pvcA)
BSTGWT74_18885 WT74_28470
PBRYNDK50_11480
AGTEYD00_23500
MAQUMaq22A_c27625
MEEDA075_00550
MTEADK419_10180
MINDmvi_13000
MLDU0023_25345 U0023_25355
FILBN1229_v1_2105
FIYBN1229_v1_2105
SECHB18_23345
PACEA6070_11560
SURSTAUR_0256(pvcA)
AGEAA314_03098 AA314_05405
BBABd1454(pvcA)
BBATBdt_1440(pvcA)
BBACEP01_03530
BDQCIK05_01005
BSTOC0V70_01910
PSTISOO65_09690
PIJQEJ31_03455 QEJ31_14485
BTROFJR70_30880
LGEC269_01330
ESSATZ33_00390
MSTOMSTO_36450(pvcA)
CCYSSAMEA4530656_2636
CLIZG7Y31_00815
CQNG7Y29_02320
NBRO3I_007385
NIEKV110_36475
NGPLTT66_00585
NSPUIFM12276_39660(pvcA)
TPRTpau_3777
SGRFSGFS_103430
SRCM271_02550
SALSSLNWT_6358
STREGZL_02117 GZL_07546
SLDT261_7381
SLCSL103_14585
SRWTUE45_01198
SRNA4G23_02272 A4G23_02288
SGSAVL59_26190
SGMGCM10017557_01810(pvcA)
SCADDN051_13680 DN051_33290
SNRSNOUR_09495 SNOUR_35375 SNOUR_38585
SALUDC74_1046
SALLSAZ_05705
SPUNBFF78_37575
SGVB1H19_07080
SALJSMD11_5635
STROSTRMOE7_05240
SLKSLUN_21725
SCYAEJ357_05730
STIRDDW44_25450
SRKFGW37_05190 FGW37_29465
SSPODDQ41_27040
SVRCP971_06750 CP971_07870
SBYH7H31_12650
SRIMCP984_10745 CP984_28330
SCHACP983_37935
SBATG4Z16_03985
SPLACP981_03705
SCYGS1361_05150
SFEUIM697_17530
SDWK7C20_00380
SAUHSU9_002815
SFBCP974_12510 CP974_12590
SMOBJ7W19_04485 J7W19_31700
SANUK7396_31920
SINEKI385_06090
SAOVG3H79_37810
SNIGHEK616_25240(pvcA)
STUDSTRTU_006553
SANTQR300_36525
SYUNMOV08_09385 MOV08_34970
SOVQZH56_30865
SCHGNRO40_12665 NRO40_12745
KAUB6264_01935 B6264_03065
KITCFP65_3111
RSARSal33209_2067(pvcA)
FRAFrancci3_2754
AABA4R43_21580
AMYYYIM_23650
PSEHXF36_24020
PHHAFB00_21845 AFB00_29825
KALKALB_6297
ALOCRK57529
PMADBAY61_18530
CROSN8J89_22515 N8J89_32275
MSAGGCM10017556_09890(pvcA)
UAMUABAM_00791 UABAM_02081
CHFKTO58_07940
HSWHsw_PA0221
FSDLXD69_13605
 » 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

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