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
XCC: XCC1212(nifS)
XCB: XC_3030
XCA: xcc-b100_3093(cefD)
XCP: XCR_1454
XAX: XACM_1285
XPE: BJD13_10100
XTH: G4Q83_19870
SML: Smlt4409
SMT: Smal_3800
BUJ: BurJV3_3836
SMZ: SMD_3984
VAG: N646_3232
PPR: PBPRB0227(SCRA)
PFL: PFL_4607
PPRO: PPC_4709
PFS: PFLU_4835
PFB: VO64_1690
PMAN: OU5_4921
PSEM: TO66_24020
PSOS: POS17_4674
PANR: A7J50_4605
PSIL: PMA3_23020
SPL: Spea_3648
SHL: Shal_3735
SWD: Swoo_4279
FBL: Fbal_3231
MVS: MVIS_3970
RSO: RSp0696
RSL: RPSI07_mp0854(cefD)
RSN: RSPO_c00320(cefD)
RSY: RSUY_02990(cefD)
CGD: CR3_3821(csdB)
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
BDL: AK34_5097
BUL: BW21_5329
PLG: NCTC10937_01176(cefD)
BUO: BRPE64_BCDS08330(sufS)
AAV: Aave_1124
AAA: Acav_1121
DAC: Daci_5319
RTA: Rta_32020
RGE: RGE_38680
MXA: MXAN_5758(cefD)
CCX: COCOR_06250(cefD)
SUR: STAUR_6423(cefD)
SCL: sce8130
BBT: BBta_3802
BARH: WN72_04450
HBA: Hbal_2708
SPHI: TS85_22675
SSAN: NX02_08215
SSY: SLG_33460
SPHR: BSY17_3059
SHUM: STHU_41780(cefD)
SVC: STVA_45250(nifS)
HTQ: FRZ44_45180(nifS)
HADH: FRZ61_42820(nifS)
BBA: Bd2034
BBAT: Bdt_2002
BBW: BDW_07330
BBAC: EP01_06195
MMAG: MMAD_03810(cefD)
SGB: WQO_32335
SCT: SCAT_5686(cefD)
SBH: SBI_00921
STRM: M444_06915
SRW: TUE45_pSRc_0626(cefD)
SMAL: SMALA_2490
SLAU: SLA_7034
SALJ: SMD11_6247
SLX: SLAV_07070(cefD2)
SFK: KY5_0714
SGE: DWG14_07627(cefD_2)
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)
ALO: CRK55303
MIL: ML5_1645
ASE: ACPL_7270(cefD)
ACTN: L083_6863(cefD)
AFS: AFR_36275
ACTS: ACWT_7140
CAI: Caci_5559
SNA: Snas_2195
BLN: Blon_1377
BLON: BLIJ_1421
BBRE: B12L_0972
BBRV: B689b_1067
BBRC: B7019_1125
BBRN: B2258_1017
BBRD: BBBR_1001
CYA: CYA_0818(cefD)
CYB: CYB_1874(cefD)
LET: O77CONTIG1_02952(cefD_2)
LBO: LBWT_6690
AMR: AM1_6324
MAR: MAE_52910
MPK: VL20_1539
NSH: GXM_02799
CALH: IJ00_06455
RCA: Rcas_3584
CAU: Caur_1659
CAG: Cagg_2502
STI: Sthe_1315
ATM: ANT_18540
MRB: Mrub_1746
RBA: RB7564(cefD)
PSL: Psta_2194
PIR: VN12_10170(cefD)
MFF: MFFC18_08200(cefD)
ROL: CA51_19080(cefD)
LCRE: Pla8534_29080(cefD)
AMUC: Pan181_34570(cefD)
PLM: Plim_1607
PEH: Spb1_24620(cefD)
PLS: VT03_15840(cefD)
FMR: Fuma_05761(cefD)
BVO: Pan97_28140(cefD)
MRI: Mal4_46350(cefD)
SDYN: Mal52_22760(cefD)
PLON: Pla110_41390(cefD)
GES: VT84_18005(cefD)
FTJ: FTUN_5065
IPA: Isop_2866
AGV: OJF2_29370(cefD)
ABAC: LuPra_01101(cefD_1) LuPra_04390(cefD_4) LuPra_06203(cefD_5)
GBA: J421_0094
FSN: GS03_01086(cefD)
 » 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

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