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

XDY:	NYR95_07600

XRY:	QN244_11760

RSO:

RSp0696

RSE:	F504_4019 F504_4523

RPU:	CDC45_21100

RNC:	GO999_17565

RSC:	RCFBP_10279

RSL:	RPSI07_mp0854(cefD)

RSN:	RSPO_c00320(cefD)

RSM:	CMR15_mp10667

RSY:	RSUY_02990(cefD)

BMA:

BMAA0692

BML:	BMA10229_0775

BMN:	BMA10247_A1739

BMAZ:

BM44_4735

BMAL:

DM55_4745

BMAE:

DM78_3245

BMAQ:

DM76_3699

BMAI:

DM57_12105

BMAF:

DM51_4398

BMAB:

BM45_4997

BPS:

BPSS0826

BPM:	BURPS1710b_A2417(cefD)

BPL:	BURPS1106A_A1140(cefD)

BPD:	BURPS668_A1215

BPR:	GBP346_B0466

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

BUD:	AQ610_26555

BUL:

BW21_5329

RGE:

RGE_38680

RBN:	RBXJA2T_10891

SMIO:

CATMQ487_06660

MPAU:

ZMTM_08360(cefD)

DEQ:	XM25_21970

DEI:	C4375_02015

DEA:	FPZ08_09510

DSAL:

K1X15_04340

DEVO:

H4N61_13030

DOY:	JI749_08445

DEVD:

GHV40_18825

DRI:	QOV41_13735

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)

THAR:

T8K17_17400

MXA:	MXAN_5758(cefD)

MSD:	MYSTI_06344

MFB:	MFUL124B02_33455

MYX:	QEG98_31635

MLAN:

JY572_35280

MYM:	A176_001151

CCX:	COCOR_06250(cefD)

MMAS:

MYMAC_005550

PPAK:

JY651_02520

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

MRM:	A7982_01717

SAMY:

DB32_008262

NANN:

O0S08_20395

LAMB:

KBB96_08940

RBA:	RB7564(cefD)

RHOI:

PSR62_08485

PSL:

Psta_2194

PIR:	VN12_10170(cefD)

RML:	FF011L_05920(cefD)

MFF:	MFFC18_08200(cefD)

ROL:	CA51_19080(cefD)

RUV:	EC9_16400(cefD)

RCF:	Poly24_22620(cefD)

LCRE:

Pla8534_29080(cefD)

AAGG:

ETAA8_46010(cefD_1)

BVO:	Pan97_28140(cefD)

BREM:

PSR63_25235

RLC:	K227x_38360(cefD)

SMAM:

Mal15_34460(cefD_2)

SNEP:

Enr13x_47230(cefD)

SMAE:

TBK1r_13780(cefD_2)

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)

ACAF:

CA12_17910(cefD)

SVP:	Pan189_33820(cefD)

TPOL:

Mal48_03320(cefD)

CHYA:

V22_06160(cefD)

CCOS:

Pan44_24230(cefD)

PVAR:

SH412_001124

SCHL:

QJS52_02530

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

PBAP:

Pla133_49220(cefD_3)

HBS:	IPV69_22455

ABAC:

LuPra_04390(cefD_4)

LUB:	TBR22_A33070(nifS)

SEDT:

TEGAF0_09370

PCAU:

HWD63_02110

AHAP:

V8V91_24645

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

PCAY:

FRD00_09290

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

STUB:

MMF93_07995

SXT:	KPP03845_106182(cefD_2)

SLON:

LGI35_03655

STEE:

F3L20_30335

SGK:	PET44_05500

SANT:

QR300_14510

SROC:

RGF97_02650

STTN:

BSL84_28655

SLUO:

PS467_14415

STII:

DRB96_21215

STIC:

DRB89_20720

SGRO:

UBV09_15500

SSLI:

R2D22_00425

SCT:	SCAT_5686(cefD)

SCY:	SCATT_56860

KSK:	KSE_61030 KSE_67160

KAU:	B6264_21240

KIT:	CFP65_1261

KIS:	HUT16_28860 HUT16_31665

KCH:	O1G21_30720

KCM:	ABWK59_28155

KNB:	ACF9IK_28075

MIM:	AKG07_10945

MIX:	AB663_000507

MIP:	AXH82_04565

MICR:

BMW26_15685

MFOL:

DXT68_15110

MOY:	CVS54_03345(cefD)

MLIQ:

NMQ05_16130

MPAO:

IZR02_15015

MAZA:

NFX31_15115

MSUW:

GCM10025863_29000

MEST:

PTQ19_13950

MAUG:

KV397_01800

MSUF:

KV394_03220

MVD:	AWU67_11780

SALA:

ESZ53_08205

PLAP:

EAO79_07900

PFLU:

BWO91_03995

LYH:	FrondiHNR_12415

ARM:

ART_1339

AAQ:	AOC05_09685

ARW:	MB46_10130

APOA:

J0916_09220

PNV:	JMY29_01460

PAYN:

HMI60_05600

BHQ:	BRM3_00490

YIM:	J5M86_05170

CELN:

CELD12_32120

ICA:	Intca_2268

PEI:	H9L10_13110

TED:	U5C87_18950

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

TLS:	QH948_00940

NMES:

H9L09_05140

SGRG:

L0C25_21415

KFL:

Kfla_3594

KQI:	F1D05_04065

KSL:	OG809_32655

KRI:	OX958_18130

SRO:

Sros_3487

NAK:	EH165_10100

KRA:

Krad_0174

AAB:	A4R43_03210

AMYY:

YIM_39195(cefD)

AAUR:

V5P93_002869

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

MCHL:

PVK74_28195

MFEU:

H1D33_13810

MPRN:

Q3V37_00100

MHAW:

RMN56_04410

MCAY:

PVK37_14095

MICF:

QQG74_07460

ASE:	ACPL_7270(cefD)

AMS:	AMIS_70160

ACTN:

L083_6863(cefD)

ACTS:

ACWT_7140

AIH:	Aiant_31070

ACTR:

Asp14428_61970

ACTL:

L3i22_095920

ASIC:

Q0Z83_099930

AOU:	ACTOB_007551

ACTE:

ACTI_10340

AFS:

AFR_36275

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

DACT:

KZZ52_07640

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)

CYN:	Cyan7425_0721

LEN:	LEP3755_56000

LET:	O77CONTIG1_02952(cefD_2)

LBO:

LBWT_6690

KOV:	K9N68_00020

LSC:	KIK02_18180

LSK:	J5X98_02080

SFRI:

RBJ76_25440

PSEU:

Pse7367_0560

THEU:

HPC62_17260

TOG:	HNI00_21275

TSIN:

OXH18_24755

MAR:

MAE_52910

MPK:

VL20_1539

MIQ:	B5D77_20865

MVZ:	myaer102_25690

CYC:	PCC7424_2941

CYJ:	Cyan7822_0165

PAGH:

NIES204_01190

PPSU:

NO713_03427(cefD)

PRUN:

PCC7821_04246(cefD)

MVAG:

D0A34_08910

CSAU:

ACL6C3_24250

OXY:	HCG48_13595

OAC:	Oscil6304_1893

ONI:	Osc7112_1264

MIC:	Mic7113_6306

GEI:	GEI7407_2493

NOS:	Nos7107_3892

NOP:	Nos7524_1419

NFL:	COO91_06390

NSH:

GXM_02799

NPZ:	ACX27_12290

NCW:	NIES2107_54930

NOST:

GJB62_21790

NOSQ:

PQG02_15020

CALT:

Cal6303_1535

CALH:

IJ00_06455

CALN:

NIES2098_14720

CALS:

NIES3974_08800

MDP:	NIES3275_41990

STOQ:

K2F26_09420

SKV:	NIES73_17550

TOQ:	HCG51_18985

TTQ:	NIES37_54700

ALAX:

NIES50_31850

SCYS:

NIES4073_38250

PLP:	Ple7327_4280

RRS:	RoseRS_1377

RCA:

Rcas_3584

CAU:

Caur_1659

CHL:	Chy400_1800

CAG:

Cagg_2502

CALL:

OZ401_003486

ATM:

ANT_18540

CAP:	CLDAP_22540

PBF:	CFX0092_A1218

KBS:	EPA93_01175

PMET:

G4Y79_02185

MRB:

Mrub_1746

MRE:	K649_13825

MTAI:

Mtai_v1c12130

» 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 JM, Martin JF.

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 WK, Ghag SK, Queener SW.

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

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Gene (8287)   
   MGENES (6645)   
   RefGene (1642)   
Protein sequence (464)   
   UniProt (458)   
   SWISS-PROT (4)   
   RefSeq(pep) (2)   
DNA sequence (723)   
   RefSeq(nuc) (4)   
   GenBank (368)   
   EMBL (351)   
Protein domain (13)   
   InterPro (13)   
All databases (9487)   

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