KEGG   ORTHOLOGY: K04127
Entry
K04127                      KO                                     
Symbol
cefD
Name
isopenicillin-N epimerase [EC:5.1.1.17]
Pathway
map00311  Penicillin and cephalosporin biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00673  Cephamycin C biosynthesis, aminoadipate + cycteine + valine => cephamycin C
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00311 Penicillin and cephalosporin biosynthesis
    K04127  cefD; isopenicillin-N epimerase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   01008 Polyketide biosynthesis proteins
    K04127  cefD; isopenicillin-N epimerase
Enzymes [BR:ko01000]
 5. Isomerases
  5.1  Racemases and epimerases
   5.1.1  Acting on amino acids and derivatives
    5.1.1.17  isopenicillin-N epimerase
     K04127  cefD; isopenicillin-N epimerase
Polyketide biosynthesis proteins [BR:ko01008]
 Nonribosomal peptide tailoring proteins
  Others
   K04127  cefD; isopenicillin-N epimerase
Other DBs
RN: R04147
GO: 0045439
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)
RSY: RSUY_02990(cefD)
BMA: BMAA0692
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)
BPSE: BDL_4112
BPSM: BBQ_5312
BPSU: BBN_4284
BPSD: BBX_5952
BPK: BBK_3615
BPSH: DR55_4511
BPSA: BBU_5206
BPSO: X996_4060
BUT: X994_3738
BTD: BTI_5642
BUL: BW21_5329
RGE: RGE_38680
MPAU: ZMTM_08360(cefD)
MXA: MXAN_5758(cefD)
CCX: COCOR_06250(cefD)
SUR: STAUR_6423(cefD)
SCL: sce8130
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
SMAL: SMALA_2490
SCT: SCAT_5686(cefD)
SBH: SBI_00921
STRM: M444_06915
SGM: GCM10017557_05590(nifS)
SLAU: SLA_7034
SLX: SLAV_07070(cefD2)
SFK: KY5_0714
SGE: DWG14_07627(cefD_2)
SNF: JYK04_06931(cefD)
MOY: CVS54_03345(cefD)
ARM: ART_1339
TLA: TLA_TLA_01558(cefD)
KFL: Kfla_3594
SRO: Sros_3487
KRA: Krad_0174
AMYY: YIM_39195(cefD)
MIL: ML5_1645
ASE: ACPL_7270(cefD)
ACTN: L083_6863(cefD)
AFS: AFR_36275
ACTS: ACWT_7140
CAI: Caci_5559
SNA: Snas_2195
CYA: CYA_0818(cefD)
CYB: CYB_1874(cefD)
LET: O77CONTIG1_02952(cefD_2)
LBO: LBWT_6690
MAR: MAE_52910
MPK: VL20_1539
NSH: GXM_02799
CALH: IJ00_06455
RCA: Rcas_3584
CAU: Caur_1659
CAG: Cagg_2502
ATM: ANT_18540
MRB: Mrub_1746
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)
PLS: VT03_15840(cefD)
FMR: Fuma_05761(cefD)
MRI: Mal4_46350(cefD)
SDYN: Mal52_22760(cefD)
PLON: Pla110_41390(cefD)
GES: VT84_18005(cefD)
FTJ: FTUN_5065
ULI: ETAA1_15630(cefD)
IPA: Isop_2866
ABAC: LuPra_04390(cefD_4)
FSN: GS03_01086(cefD)
AG: AAA26714(cefD)
 » show all
Reference
PMID:1694525
  Authors
Kovacevic S, Tobin MB, Miller JR
  Title
The beta-lactam biosynthesis genes for isopenicillin N epimerase and deacetoxycephalosporin C synthetase are expressed from a single transcript in Streptomyces clavuligerus.
  Journal
J Bacteriol 172:3952-8 (1990)
DOI:10.1128/JB.172.7.3952-3958.1990
  Sequence

KEGG   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
XCCXCC1212(nifS)
XCBXC_3030
XCAxcc-b100_3093(cefD)
XCPXCR_1454
XAXXACM_1285
XPEBJD13_10100
RSORSp0696
RSCRCFBP_10279
RSLRPSI07_mp0854(cefD)
RSNRSPO_c00320(cefD)
RSMCMR15_mp10667
RSEF504_4019 F504_4523
RSYRSUY_02990(cefD)
RPUCDC45_21100
BMABMAA0692
BMLBMA10229_0775
BMNBMA10247_A1739
BMALDM55_4745
BMAEDM78_3245
BMAQDM76_3699
BMAIDM57_12105
BMAFDM51_4398
BMAZBM44_4735
BMABBM45_4997
BPSBPSS0826
BPMBURPS1710b_A2417(cefD)
BPLBURPS1106A_A1140(cefD)
BPDBURPS668_A1215
BPSEBDL_4112
BPSMBBQ_5312
BPSUBBN_4284
BPSDBBX_5952
BPZBP1026B_II0908
BPQBPC006_II1157
BPKBBK_3615
BPSHDR55_4511
BPSABBU_5206
BPSOX996_4060
BUTX994_3738
BTDBTI_5642
BULBW21_5329
BUDAQ610_26555
RGERGE_38680
RBNRBXJA2T_10891
MPAUZMTM_08360(cefD)
MXAMXAN_5758(cefD)
MSDMYSTI_06344
MYMA176_001151
MFBMFUL124B02_33455
CCXCOCOR_06250(cefD)
MMASMYMAC_005550
SURSTAUR_6423(cefD)
AGEAA314_08250
AVMJQX13_27415
MBDMEBOL_001410
CFUSCYFUS_008015
SCLsce8130
SCUSCE1572_47340
CCROCMC5_004080
SAMYDB32_008262
MRMA7982_01717
PCAYFRD00_09290
DEQXM25_21970
DEIC4375_02015
DEAFPZ08_09510
DSALK1X15_04340
YTIFNA67_03420
MEYTM49_09960
PPAFI8N54_06570
CBOTATE48_18515
SHUMSTHU_41780(cefD)
SVCSTVA_45250(nifS)
STELSTAQ_06800(nifS_2)
HTQFRZ44_45180(nifS)
HADHFRZ61_42820(nifS)
MMAGMMAD_03810(cefD)
SGBWQO_32335
SVLStrvi_7696
SRCM271_39675
SMALSMALA_2490
SSOII1A49_15905
SCTSCAT_5686(cefD)
SCYSCATT_56860
SBHSBI_00921
STRMM444_06915
SCXAS200_38920
STRFASR50_18190
STRTA8713_30255
SCLFBB341_07745
SGMGCM10017557_05590(nifS)
SCADDN051_04840
SAUOBV401_15975
SLAUSLA_7034
SLXSLAV_07070(cefD2)
SFKKY5_0714
SNZDC008_32885
SGEDWG14_07627(cefD_2)
SCYAEJ357_00895
SASTCD934_13720
STIRDDW44_23120
SKACP970_39425
SGZC0216_11470
SVNCP980_05600
SVRCP971_26680
SSUBCP968_06165
SFUGCNQ36_15950
SCHACP983_42365
SGXH4W23_37025
SNFJYK04_06931(cefD)
SCHFIPT68_00485
SFEUIM697_21765
SPRACP972_16780
KSKKSE_61030 KSE_67160
KAUB6264_21240
KITCFP65_1261
MIMAKG07_10945
MIXAB663_000507
MIPAXH82_04565
MICRBMW26_15685
MFOLDXT68_15110
MOYCVS54_03345(cefD)
MVDAWU67_11780
SALAESZ53_08205
PLAPEAO79_07900
ARMART_1339
AAQAOC05_09685
ARWMB46_10130
PNVJMY29_01460
YIMJ5M86_05170
ICAIntca_2268
PEIH9L10_13110
SERWFY030_12905
HALTIM660_18840
MIKFOE78_15590
MICGGJV80_09610
TEZBKM78_07710
TLATLA_TLA_01558(cefD)
NMESH9L09_05140
KFLKfla_3594
KQIF1D05_04065
SROSros_3487
NAKEH165_10100
KRAKrad_0174
AABA4R43_03210
AMYYYIM_39195(cefD)
MAUMicau_1400
MILML5_1645
MICBMicB006_1421
MTUACSH63_17225
MICHFJK98_07455
MTEMGCE86_01155
MCABHXZ27_08180
MSAGGCM10017556_39760
VMAVAB18032_11635
MCRAID554_04995
ASEACPL_7270(cefD)
AMSAMIS_70160
ACTNL083_6863(cefD)
AFSAFR_36275
ACTSACWT_7140
AIHAiant_31070
PLKCIK06_07210
PLABC6361_16300
PLATC6W10_13995
PFLAPflav_086350
PSUUPsuf_049280 Psuf_059680
VERHUT12_07990
ATLAthai_23090
ASERAsera_51820
PRYPrubr_39970
CATICS0771_23670
DVCDvina_08360
CAICaci_5559
SNASnas_2195
MCUHMPREF0573_11857
BSCABBSC_0334 BBSC_0361
CYACYA_0818(cefD)
CYBCYB_1874(cefD)
LENLEP3755_56000
LETO77CONTIG1_02952(cefD_2)
LBOLBWT_6690
KOVK9N68_00020
LSCKIK02_18180
LSKJ5X98_02080
PSEUPse7367_0560
THEUHPC62_17260
MARMAE_52910
MPKVL20_1539
MIQB5D77_20865
MVZmyaer102_25690
CYCPCC7424_2941
CYJCyan7822_0165
CYNCyan7425_0721
PAGHNIES204_01190
OXYHCG48_13595
MVAGD0A34_08910
MICMic7113_6306
GEIGEI7407_2493
OACOscil6304_1893
ONIOsc7112_1264
NOSNos7107_3892
NOPNos7524_1419
NFLCOO91_06390
NSHGXM_02799
CALTCal6303_1535
CALHIJ00_06455
TOQHCG51_18985
PLPPle7327_4280
RRSRoseRS_1377
RCARcas_3584
CAUCaur_1659
CHLChy400_1800
CAGCagg_2502
ATMANT_18540
CAPCLDAP_22540
PBFCFX0092_A1218
KBSEPA93_01175
PMETG4Y79_02185
MRBMrub_1746
MREK649_13825
MTAIMtai_v1c12130
LAMBKBB96_08940
RBARB7564(cefD)
PSLPsta_2194
PIRVN12_10170(cefD)
RMLFF011L_05920(cefD)
MFFMFFC18_08200(cefD)
ROLCA51_19080(cefD)
LCREPla8534_29080(cefD)
AAGGETAA8_46010(cefD_1)
BVOPan97_28140(cefD)
RLCK227x_38360(cefD)
AMUCPan181_34570(cefD)
PLMPlim_1607
PEHSpb1_24620(cefD)
PBSPlabr_2872
PLSVT03_15840(cefD)
FMRFuma_05761(cefD)
MRIMal4_46350(cefD)
SDYNMal52_22760(cefD)
PLONPla110_41390(cefD)
GESVT84_18005(cefD)
GOGC1280_18815
GMSSOIL9_20600
TIMGMBLW1_51170
LRSPX52LOC_01421
FTJFTUN_5065
ULIETAA1_15630(cefD)
TSPHKIH39_02625
IPAIsop_2866
HBSIPV69_22455
ABACLuPra_04390(cefD_4)
FBRFBFL15_2075
FPALHYN49_06285
FMGHYN48_05940
FSNGS03_01086(cefD)
FNKE1750_07650
FTEFluta_3137
FLUCHH17_06265
CRMK6119_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
Reference
2
  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
4
  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

KEGG   REACTION: R04147
Entry
R04147                      Reaction                               
Definition
Isopenicillin N <=> Penicillin N
Equation
Reaction class
RC00302  C05557_C06564
Enzyme
Pathway
rn00311  Penicillin and cephalosporin biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00673  Cephamycin C biosynthesis, aminoadipate + cycteine + valine => cephamycin C
Orthology
K04127  isopenicillin-N epimerase [EC:5.1.1.17]
Other DBs
RHEA: 20036

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