KEGG ENZYME: 4.1.99.24

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

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

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)

PAP:	PSPA7_2987(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

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)

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

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

SECH:

B18_23345

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

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

KAU:	B6264_01935 B6264_03065

KIT:	CFP65_3111

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)

UAM:	UABAM_00791 UABAM_02081

CHF:	KTO58_07940

HSW:	Hsw_PA0221

FSD:	LXD69_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

DBGET integrated database retrieval system