KEGG ENZYME: 5.1.1.17

ENZYME: 5.1.1.17

Entry

EC 5.1.1.17                 Enzyme

Name

isopenicillin-N epimerase

Class

Isomerases;
Racemases and epimerases;
Acting on amino acids and derivatives

Sysname

penicillin-N 5-amino-5-carboxypentanoyl-epimerase

Reaction(IUBMB)

isopenicillin N = penicillin N [RN:R04147]

Reaction(KEGG)

R04147

Substrate

isopenicillin N [CPD:C05557]

Product

penicillin N [CPD:C06564]

Comment

This enzyme contains pyridoxal phosphate. Epimerization at C-5 of the 5-amino-5-carboxypentanoyl group to form penicillin N is required to make a substrate for EC 1.14.20.1, deactoxycephalosporin-C synthase, to produce cephalosporins. Forms part of the penicillin biosynthesis pathway (for pathway, click here).

History

EC 5.1.1.17 created 2002

Pathway

ec00311

Penicillin and cephalosporin biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K04127

isopenicillin-N epimerase

Genes

XCC:	XCC1212(nifS)

XCB:

XC_3030

XCA:	xcc-b100_3093(cefD)

XCP:

XCR_1454

XAX:

XACM_1285

XPE:	BJD13_10100

RSO:

RSp0696

RSC:	RCFBP_10279

RSL:	RPSI07_mp0854(cefD)

RSN:	RSPO_c00320(cefD)

RSM:	CMR15_mp10667

RSE:	F504_4019 F504_4523

RSY:	RSUY_02990(cefD)

RPU:	CDC45_21100

BMA:

BMAA0692

BML:	BMA10229_0775

BMN:	BMA10247_A1739

BMAL:

DM55_4745

BMAE:

DM78_3245

BMAQ:

DM76_3699

BMAI:

DM57_12105

BMAF:

DM51_4398

BMAZ:

BM44_4735

BMAB:

BM45_4997

BPS:

BPSS0826

BPM:	BURPS1710b_A2417(cefD)

BPL:	BURPS1106A_A1140(cefD)

BPD:	BURPS668_A1215

BPSE:

BDL_4112

BPSM:

BBQ_5312

BPSU:

BBN_4284

BPSD:

BBX_5952

BPZ:	BP1026B_II0908

BPQ:	BPC006_II1157

BPK:

BBK_3615

BPSH:

DR55_4511

BPSA:

BBU_5206

BPSO:

X996_4060

BUT:

X994_3738

BTD:

BTI_5642

BHG:	I6G56_23855

BUL:

BW21_5329

BUD:	AQ610_26555

RGE:

RGE_38680

RBN:	RBXJA2T_10891

MPAU:

ZMTM_08360(cefD)

MXA:	MXAN_5758(cefD)

MSD:	MYSTI_06344

MYM:	A176_001151

MFB:	MFUL124B02_33455

CCX:	COCOR_06250(cefD)

MMAS:

MYMAC_005550

SUR:	STAUR_6423(cefD)

AGE:	AA314_08250

AVM:	JQX13_27415

MBD:	MEBOL_001410

CFUS:

CYFUS_008015

SCL:

sce8130

SCU:	SCE1572_47340

CCRO:

CMC5_004080

PAUU:

E8A73_014625

SAMY:

DB32_008262

MRM:	A7982_01717

NANN:

O0S08_20395

PCAY:

FRD00_09290

DEQ:	XM25_21970

DEI:	C4375_02015

DEA:	FPZ08_09510

DSAL:

K1X15_04340

DEVO:

H4N61_13030

YTI:	FNA67_03420

MEY:	TM49_09960

PPAF:

I8N54_06570

CBOT:

ATE48_18515

RAP:

RHOA_1134

SHUM:

STHU_41780(cefD)

SVC:	STVA_45250(nifS)

STEL:

STAQ_06800(nifS_2)

HTQ:	FRZ44_45180(nifS)

HADH:

FRZ61_42820(nifS)

MMAG:

MMAD_03810(cefD)

SGB:

WQO_32335

SVL:	Strvi_7696

SRC:	M271_39675

SMAL:

SMALA_2490

SSOI:

I1A49_15905

SBH:

SBI_00921

STRM:

M444_06915

SCX:	AS200_38920

STRF:

ASR50_18190

STRT:

A8713_30255

SCLF:

BB341_07745

SGM:	GCM10017557_05590(nifS)

SCAD:

DN051_04840

SPHW:

NFX46_16550

SAUO:

BV401_15975

SLAU:

SLA_7034

SLX:	SLAV_07070(cefD2)

SFK:

KY5_0714

SNZ:	DC008_32885

SGE:	DWG14_07627(cefD_2)

SCYA:

EJ357_00895

SAST:

CD934_13720

STIR:

DDW44_23120

SKA:	CP970_39425

SGZ:	C0216_11470

SVN:	CP980_05600

SVR:	CP971_26680

SSUB:

CP968_06165

SFUG:

CNQ36_15950

SCHA:

CP983_42365

SGX:	H4W23_37025

SNF:	JYK04_06931(cefD)

SCHF:

IPT68_00485

SFEU:

IM697_21765

SPRA:

CP972_16780

SLF:	JEQ17_04340

SYAN:

NRK68_29015

STAA:

LDH80_35675

SCT:	SCAT_5686(cefD)

SCY:	SCATT_56860

KSK:	KSE_61030 KSE_67160

KAU:	B6264_21240

KIT:	CFP65_1261

KIS:	HUT16_28860 HUT16_31665

MIM:	AKG07_10945

MIX:	AB663_000507

MIP:	AXH82_04565

MICR:

BMW26_15685

MFOL:

DXT68_15110

MOY:	CVS54_03345(cefD)

MLIQ:

NMQ05_16130

MVD:	AWU67_11780

SALA:

ESZ53_08205

PLAP:

EAO79_07900

ARM:

ART_1339

AAQ:	AOC05_09685

ARW:	MB46_10130

APOA:

J0916_09220

PNV:	JMY29_01460

BHQ:	BRM3_00490

YIM:	J5M86_05170

ICA:	Intca_2268

PEI:	H9L10_13110

SERW:

FY030_12905

HALT:

IM660_18840

RHAL:

LQF10_18445

RSUA:

LQF12_15750

MIK:	FOE78_15590

MICG:

GJV80_09610

TEZ:	BKM78_07710

TLA:	TLA_TLA_01558(cefD)

TEJ:	KDB89_13755

NMES:

H9L09_05140

KFL:

Kfla_3594

KQI:	F1D05_04065

SRO:

Sros_3487

NAK:	EH165_10100

KRA:

Krad_0174

AAB:	A4R43_03210

AMYY:

YIM_39195(cefD)

MAU:	Micau_1400

MIL:

ML5_1645

MICB:

MicB006_1421

MTUA:

CSH63_17225

MICH:

FJK98_07455

MTEM:

GCE86_01155

MCAB:

HXZ27_08180

MSAG:

GCM10017556_39760

VMA:	VAB18032_11635

MCRA:

ID554_04995

VER:	HUT12_07990

ASE:	ACPL_7270(cefD)

AMS:	AMIS_70160

ACTN:

L083_6863(cefD)

AFS:

AFR_36275

ACTS:

ACWT_7140

AIH:	Aiant_31070

ACTR:

Asp14428_61970

PLK:	CIK06_07210

PLAB:

C6361_16300

PLAT:

C6W10_13995

PFLA:

Pflav_086350

PSUU:

Psuf_049280 Psuf_059680

ATL:	Athai_23090

ASER:

Asera_51820

PRY:	Prubr_39970

CATI:

CS0771_23670

DVC:	Dvina_08360

DFU:	Dfulv_07810

DROS:

Drose_08095

DAUR:

Daura_07780

DMAT:

Dmats_07870

CCAZ:

COUCH_08195

CAI:

Caci_5559

SNA:

Snas_2195

MCU:	HMPREF0573_11857

BSCA:

BBSC_0334 BBSC_0361

CYA:	CYA_0818(cefD)

CYB:	CYB_1874(cefD)

LEN:	LEP3755_56000

LET:	O77CONTIG1_02952(cefD_2)

LBO:

LBWT_6690

KOV:	K9N68_00020

LSC:	KIK02_18180

LSK:	J5X98_02080

PSEU:

Pse7367_0560

THEU:

HPC62_17260

MAR:

MAE_52910

MPK:

VL20_1539

MIQ:	B5D77_20865

MVZ:	myaer102_25690

CYC:	PCC7424_2941

CYJ:	Cyan7822_0165

CYN:	Cyan7425_0721

PAGH:

NIES204_01190

PPSU:

NO713_03427(cefD)

OXY:	HCG48_13595

MVAG:

D0A34_08910

MIC:	Mic7113_6306

GEI:	GEI7407_2493

OAC:	Oscil6304_1893

ONI:	Osc7112_1264

NOS:	Nos7107_3892

NOP:	Nos7524_1419

NFL:	COO91_06390

NSH:

GXM_02799

CALT:

Cal6303_1535

CALH:

IJ00_06455

CALN:

NIES2098_14720

TOQ:	HCG51_18985

PLP:	Ple7327_4280

RRS:	RoseRS_1377

RCA:

Rcas_3584

CAU:

Caur_1659

CHL:	Chy400_1800

CAG:

Cagg_2502

ATM:

ANT_18540

CAP:	CLDAP_22540

PBF:	CFX0092_A1218

KBS:	EPA93_01175

PMET:

G4Y79_02185

MRB:

Mrub_1746

MRE:	K649_13825

MTAI:

Mtai_v1c12130

LAMB:

KBB96_08940

RBA:	RB7564(cefD)

PSL:

Psta_2194

PIR:	VN12_10170(cefD)

RML:	FF011L_05920(cefD)

MFF:	MFFC18_08200(cefD)

ROL:	CA51_19080(cefD)

LCRE:

Pla8534_29080(cefD)

AAGG:

ETAA8_46010(cefD_1)

BVO:	Pan97_28140(cefD)

RLC:	K227x_38360(cefD)

AMUC:

Pan181_34570(cefD)

PLM:

Plim_1607

PEH:	Spb1_24620(cefD)

PBS:	Plabr_2872

PLS:	VT03_15840(cefD)

FMR:	Fuma_05761(cefD)

MRI:	Mal4_46350(cefD)

SDYN:

Mal52_22760(cefD)

PLON:

Pla110_41390(cefD)

GES:	VT84_18005(cefD)

GOG:	C1280_18815

GMS:	SOIL9_20600

TIM:	GMBLW1_51170

LRS:	PX52LOC_01421

FTJ:

FTUN_5065

ULI:	ETAA1_15630(cefD)

TSPH:

KIH39_02625

IPA:

Isop_2866

HBS:	IPV69_22455

ABAC:

LuPra_04390(cefD_4)

SEDT:

TEGAF0_09370

FBR:	FBFL15_2075

FPAL:

HYN49_06285

FMG:	HYN48_05940

FSN:	GS03_01086(cefD)

FNK:	E1750_07650

FSD:	LXD69_03430

FTE:	Fluta_3137

FLU:	CHH17_06265

CRM:	K6119_12295

» show all

Reference

1 [PMID:2804141]

Authors

Usui S, Yu CA

Title

Purification and properties of isopenicillin N epimerase from Streptomyces clavuligerus.

Journal

Biochim Biophys Acta 999:78-85 (1989)
DOI:10.1016/0167-4838(89)90033-2

Sequence

[ag:AAA26714]

Reference

Authors

Laiz, L., Liras, P., Castro, J.M. and Martin, J.F.

Title

Purification and characterization of the isopenicillin-N epimerase from Nocardia lactamdurans.

Journal

J Gen Microbiol 136:663-671 (1990)

Reference

3 [PMID:1354366]

Authors

Cantwell C, Beckmann R, Whiteman P, Queener SW, Abraham EP.

Title

Isolation of deacetoxycephalosporin C from fermentation broths of Penicillium chrysogenum transformants: construction of a new fungal biosynthetic pathway.

Journal

Proc R Soc Lond B Biol Sci 248:283-9 (1992)
DOI:10.1098/rspb.1992.0073

Reference

Authors

Yeh, W.K., Ghag, S.K. and Queener, S.W.

Title

Enzymes for epimerization of isopenicillin N, ring expansion of penicillin N, and 3'-hydroxylation of deacetoxycephalosporin C. Function, evolution, refolding, and enzyme engineering.

Journal

Ann NY Acad Sci 672:396-408 (1992)

Other DBs

ExplorEnz - The Enzyme Database:

5.1.1.17

IUBMB Enzyme Nomenclature:

5.1.1.17

ExPASy - ENZYME nomenclature database:

5.1.1.17

BRENDA, the Enzyme Database:

5.1.1.17

CAS:	88201-43-8

DBGET integrated database retrieval system