KEGG   ENZYME: 6.1.3.1
Entry
EC 6.1.3.1                  Enzyme                                 
Name
olefin beta-lactone synthetase;
oleC (gene name)
Class
Ligases;
Forming carbon-oxygen bonds;
Cyclo-ligases
Sysname
(2R,3S)-2-alkyl-3-hydroxyalkanoate ligase (beta-lactone,AMP-forming)
Reaction(IUBMB)
ATP + a (2R,3S)-2-alkyl-3-hydroxyalkanoate = AMP + diphosphate + a cis-3-alkyl-4-alkyloxetan-2-one [RN:R11775]
Reaction(KEGG)
R11775
Substrate
ATP [CPD:C00002];
(2R,3S)-2-alkyl-3-hydroxyalkanoate [CPD:C21645]
Product
AMP [CPD:C00020];
diphosphate [CPD:C00013];
cis-3-alkyl-4-alkyloxetan-2-one [CPD:C21657]
Comment
The enzyme, found in certain bacterial species, participates in a pathway for the production of olefins. It forms a beta-lactone. The alkyl group at C2 of the substrate ends up as the 3-alkyl group of the product.
History
EC 6.1.3.1 created 2017
Orthology
K22319  olefin beta-lactone synthetase
K25044  cis-3-alkyl-4-acyloxetan-2-one decarboxylase / olefin beta-lactone synthetase
Genes
KCOBWI95_06495
KOTEH164_03280
PLUplu4510
PLUMA4R40_22330
PAYPAU_04013
PTTVY86_10480
PAKHB0X70_22720
PLUICE143_22760
PRAGEKN56_16240
XFAXF_2276
XFTPD_1311
XFMXfasm12_1468
XFNXfasM23_1395
XFFXFLM_00650
XFLP303_06255
XFSD934_06110
XFHXFHB_08780
XTWAB672_07520
XCCXCC0218
XCBXC_0228
XCAxcc-b100_0237
XCPXCR_4305
XCVXCV0243
XAXXACM_0223
XACXAC0237
XCIXCAW_00635(caiC)
XCTJ151_00354
XCJJ158_00352
XCUJ159_00352
XCNJ169_00350
XCWJ162_00351
XCRJ163_00351
XCMJ164_00351
XCFJ172_00345
XFUXFF4834R_chr02080
XAOXAC29_01220
XOMXOO3984(XOO3984)
XOOXOO4215(CaiC)
XOPPXO_03950
XOYAZ54_02865
XORXOC_0333
XOZBE73_22755
XALXALC_3069
XSASB85_13820
XTNFD63_01120
XFRBER92_17850
XVEBJD12_13760
XPEBJD13_15865
XHRXJ27_16870
XGABI317_23595
XPHXppCFBP6546_10730(XppCFBP6546P_10730)
XVAC7V42_01020
XANAC801_01010
XARXB05_17870
XHYFZ025_08640
XCZEBN15_19065
XTHG4Q83_18975
XEUXSP_000239(oleC)
XHDLMG31886_02570(oleC)
XPRMUG10_09135
SMLSmlt0208
SMTSmal_0170
BUJBurJV3_0162
SMZSMD_0178
SACZAOT14_35100
STEKAXG53_15315
SRHBAY15_0301
SLMBIZ42_10300
STENCCR98_00915
STEMCLM74_00925
STESMG068_00780
SINCDAIF1_01820(lcfB)
SPAQSTNY_R02120
PSUPsesu_0125
PSUWWQ53_07285
PSDDSC_15430
PMEXH4W19_13910
PJPLAG73_18680
PDDMNQ95_05840
LABLA76x_4682
LAQGLA29479_4477
LCPLC55x_0359
LGULG3211_0384
LEZGLE_0202
LEMLEN_4733
LMBC9I47_0307
LYTDWG18_14360
LUEDCD74_09630
LYJFKV23_00855
LSOLGOY17_18050
LSXH8B22_06705
LAREHIV01_014685
LHXLYSHEL_13660
LCASLYSCAS_13660
LCICINQ41_12450
LAVIINQ42_12080
LLZLYB30171_00152(oleC)
LUMCNR27_02290
LUSE5843_01180
LUGFPZ22_06720
THESFHQ07_09325
THEHG7079_01940
TCNH9L16_04220
XBAC7S18_19960 C7S18_19980
VTAA1844
PPRPBPRA1464(XF2276)
SONSO_1744(oleC)
SDNSden_1371
SFRSfri_1367
SAZSama_1184
SBLSbal_1552
SBMShew185_1548
SBNSbal195_1582
SBPSbal223_2798
SBTSbal678_1619
SBSSbal117_1659
SBBSbal175_2780
SLOShew_1715
SPCSputcn32_1447
SHPSput200_1460
SSESsed_1512
SPLSpea_2734
SHEShewmr4_2546
SHMShewmr7_2613
SHNShewana3_2713
SHWSputw3181_2652
SHLShal_2818
SWDSwoo_3157
SWPswp_3334
SVOSVI_3043
SHFCEQ32_07535
SJASJ2017_1517
SPSWSps_01975
SBJCF168_07315
SMAVCFF01_10785
SHEWCKQ84_00025
SLJEGC82_14490
SMAIEXU30_02220
SPOLFH971_12835
SBKSHEWBE_2083
SKHSTH12_00743(lcfB)
SAESHBH39_06150
SLITJQC75_05805
SCAATUM17387_25560(oleC)
SPSHFM037_19440
SEURFM038_007255
SCYPJYB88_06040
SSEMJYB85_06335
SGLAFJ709_06000
SINVK8B83_10015
SXMMKD32_13215
SVMKDH10_001505
SHEJMZ182_06925
CPSCPS_2155
COMCMT41_10375
PINPing_1999
PSYPCNPT3_05860
MVSMVIS_1673
MYAMORIYA_1232
WMAWM2015_2415
WEZIC757_04070
GAIIMCC3135_24165(acsA_2)
OAIOLEAN_C17450
GSNYC6258_05097
SVASVA_3744
GPBHDN1F_02410
GEMGM21_2118
GEBGM18_2132
GURGura_2008
GEOGeob_3151
GLOGlov_2271
GBMGbem_2100
GBNGEOBRER4_19300(oleC)
GERKP004_09505
GSUBKP001_05690
GNTKP003_08910
GPLM1B72_11265
PACEA6070_07235
PPDPpro_3117
DESDSOUD_2644 DSOUD_3292
DPSDP2631
DSFUWK_02995
DPRDespr_2659
DEOCAY53_08365
DOGHP555_05660
DBKDGMP_15670
DOLDole_2010
DMLDmul_23320
DATHRM2_21830
DTOTOL2_C24940
DOVDSCO28_06020
DWDDSCW_10490
DALKDSCA_08770
DLIdnl_18050
DMMdnm_089040
VINAKJ08_2416
SAMYDB32_004416
BBAEFRD01_10185
BOSBSY19_2101
BVVBHK69_25825
LABRCHH27_07235
CEHCEW89_09480
MALUKU6B_29510
HATRC74_12640
LSALKBK07_03025
RBGBG454_14940
PSEBEOK75_04325
BBABd3151
BBATBdt_3081
BBACEP01_01055
BDZDOM22_00485
BMXBMS_0542 BMS_1439
HAXBALOs_1168 BALOs_1696
BSTOC0V70_08410 C0V70_09530
BLRBRLA_c023870
BRWGOP56_04755
CLEClole_3974
CEWEKH84_01180
MVAMvan_1080
MPSCMPSYJ_00370
NFANFA_34570
NFRERS450000_00593(fcbA2)
NCYNOCYR_2360
NBRO3I_027200
NNONONO_c19430
NSLBOX37_16880
NSRNS506_01611(lys2) NS506_05575(entE)
NTPCRH09_11565 CRH09_29055
NOZDMB37_06255
NODFOH10_01645 FOH10_07005
NAHF5544_27070
NADNCTC11293_03166(fadD_3)
NIEKV110_26590
NTCKHQ06_10845 KHQ06_28980
NHUH0264_10050 H0264_19100 H0264_35200
NYALTV02_06160 LTV02_22790
NGPLTT66_26470
RHWBFN03_19170
RRZCS378_18560
RTMG4H71_11405 G4H71_18410
GITC6V83_16555
SAMBSAM23877_7350
STRDNI25_11220
SGVB1H19_06240
SLKSLUN_02580
STIRDDW44_00195
SGZC0216_32115
SHAWCEB94_37340
SSPODDQ41_00075
SPACB1H29_01570
SCOECP976_38585
SNFJYK04_07455(ppsA_2)
SVDCP969_29065
SAUHSU9_001780
KITCFP65_7006
STRIC7M71_028200
LXLKDY119_02264(oleC)
PSICJ4E96_06840
CMICMM_2154
CMSCMS1847
CMCCMN_02121
CMHVO01_10020
CCAPAES38_10520
CZHH9X71_10915
CPHAFGI33_02335
MTSMTES_0536
MCWA8L33_02695
MPALBO218_00780
MIHBJP65_04545
MLVCVS47_00573(acs)
MWAE4K62_15620
MLZF6J85_14990
MCHNHCR76_03795
MICSC1N74_10465
RTXTI83_10140
RTCAPU90_06920
RTNA6122_2397
RRYC1O28_10935
RIAC7V51_14965
RFSC1I64_12805
RTEGSU10_02655
CUMNI26_13035
CUBBJK06_11650
CUGC1N91_13450
CQFGBG65_03450
CARTPA27867_0153
CRYB7495_00675
MALKMalAC0309_0666
MYLC3E77_02030
SALAESZ53_01600
SALDFVA74_09115
PLAPEAO79_05140
MANTBHD05_11890
FRNF1C15_06375
AGXAGREI_0631
SUBTKPL76_12535
ARRARUE_c21520
ARMART_1189
ARLAFL94_04865
AREAL755_14780
AAQAOC05_09355
ARWMB46_09740
ARYATC04_12985
ARQBWQ92_22595
ACRYAC20117_20160
ARTPE5206_10070
AAGINCTC2676_1_01688(dhaA)
AJGKKR91_11275
ASUNKG104_12080
ASUFMNQ99_08600
AAUAAur_1999
PNVJMY29_09450
ACHAchl_0447
PSNINIBR502771_13170
AAIAARI_10560
GARAOZ07_05530
GCRGcLGCM259_0859
GLUF0M17_05205
GPRJQN66_05305
KRHKRH_10510
KPLKPaMU14_04550
KFVAS188_12305
KIIKocCE7_05290
KRSEQG70_07615
KODHBK84_05450
KVRCIB50_0002123(hcl)
MLUMlut_13240
MICKB1A86_00006575
MYUM8233_06345
RMURMDY18_08250
RDNHMPREF0733_12128
RAJRA11412_2077
RTERIDM49_05045
RAMAIDM48_05220
RKRI6G21_10205
SATKSA2016_3972
NAEBHE16_01725
PAEYKUF55_10280
BFABfae_17450
BRXBH708_04345
BRVCFK39_01160
BGGCFK41_08045
BRZCFK38_10145
BSAUDWV08_06125
BRRC1N80_10325
BRHANLU66_11215
DVADAD186_09750
DJJCOP05_06025
KSEKsed_07150
IVAIsova_0150
IDOI598_2611(lcfB_2)
SKESked_36600
CELZE5225_13970
SERJSGUI_1320
SERWFY030_02625
ORNDV701_15455
ORZFNH13_16510
BLYA2T55_16615
BLINBLSMQ_3614
BRIFDF13_04815
BLUTEW640_09555
BCAUI6G59_02570
DCOSAMEA4475696_0223(fcbA2)
GEZFE251_10285
GYUFE374_10105
RHALLQF10_10370
RSUALQF12_09165
MPHMLP_50960
MIKFOE78_05610
NMESH9L09_18015
NAQUENKNEFLB_01767(lcfB_2)
THAONI17_004920
ACTWF7P10_02415 F7P10_03860
NOABKM31_21640 BKM31_45965
NOWGBF35_34575
NCXNocox_12435(fcbA2)
NGNLCN96_30350
NMLNamu_4241
NAKEH165_06745
GOBGobs_2462
MMARMODMU_2228
KRAKrad_1681
SSYIEKG83_13730 EKG83_21815
MCRAID554_00400
VERHUT12_12060
AYMYM304_23880
LEPLepto7376_3112
LETO77CONTIG1_02654(ppsB)
THEUHPC62_01250
CAUCaur_3531
CHLChy400_3808
CAGCagg_0550
DMRDeima_1162
OTEOter_0858
OBGVerru16b_01069(lcfB)
VBHCMV30_08290
OLEK0B96_17285
OBTOPIT5_15255
CAACaka_2478
RUFIK0V07_03255
LUOHHL09_01900
SOAG3M56_010125
VBAIMCC26134_13705
RBARB6755
PSLPsta_3186
PIRVN12_12860(lcfB_2)
RULUC8_02000(lcfB_1) UC8_55580(lcfB_4)
RMLFF011L_43350(lcfB_3)
MFFMFFC18_05180(lcfB)
ROLCA51_33340(lcfB_2)
AHELQ31a_62570(lcfB_2)
LCREPla8534_65900(lcfB_7)
AAGGETAA8_05770(lcfB_1)
BVOPan97_33070(lcfB_1)
RLCK227x_27860(lcfB_3)
LPAVPLANPX_1005
AMUCPan181_12840(lcfB_1) Pan181_45030(lcfB_2)
PNDPla175_41180(lcfB_2)
AMOBHG15A2_09770(lcfB)
PLMPlim_3597
PEHSpb1_03150(lcfB)
PBSPlabr_4645
PLSVT03_04305(lcfB_1)
PLHVT85_06220(lcfB)
FMRFuma_03576
GMRGmarT_20650
GIMF1728_04060
GPNPan110_20020
MRIMal4_34130
SDYNMal52_34860
PLONPla110_31360(lcfB)
GESVT84_31315(lcfB_2)
GOGC1280_33740
GMSSOIL9_84920
TIMGMBLW1_07540
LRSPX52LOC_02051
FTJFTUN_1523
ULIETAA1_49620(fadD)
TSPHKIH39_05440
IPAIsop_1050
SACISinac_3642
PBORBSF38_04650(lcfB)
AGVOJF2_56800(lcfB_2)
UAMUABAM_06729
SCORJ3U87_32895
GBAJ421_1812
FIBA6C57_02925
HYMN008_12480
HYPA0257_05740
HYHD3Y59_01415
HRSHER32_04775
HTSHMJ29_00775
HTBMTX78_22430
MTTFtrac_1632
FBTD770_13490
NOJEJ995_12065
ANPFK178_13400
FLUCHH17_07910
NLIG3M70_12745
 » show all
Reference
1  [PMID:20418444]
  Authors
Sukovich DJ, Seffernick JL, Richman JE, Hunt KA, Gralnick JA, Wackett LP
  Title
Structure, function, and insights into the biosynthesis of a head-to-head hydrocarbon in Shewanella oneidensis strain MR-1.
  Journal
Appl Environ Microbiol 76:3842-9 (2010)
DOI:10.1128/AEM.00433-10
  Sequence
[son:SO_1744]
Reference
2  [PMID:20823539]
  Authors
Frias JA, Goblirsch BR, Wackett LP, Wilmot CM
  Title
Cloning, purification, crystallization and preliminary X-ray diffraction of the OleC protein from Stenotrophomonas maltophilia involved in head-to-head hydrocarbon biosynthesis.
  Journal
Acta Crystallogr Sect F Struct Biol Cryst Commun 66:1108-10 (2010)
DOI:10.1107/S1744309110031751
Reference
3  [PMID:27238740]
  Authors
Kancharla P, Bonnett SA, Reynolds KA
  Title
Stenotrophomonas maltophilia OleC-Catalyzed ATP-Dependent Formation of Long-Chain Z-Olefins from 2-Alkyl-3-hydroxyalkanoic Acids.
  Journal
Chembiochem 17:1426-9 (2016)
DOI:10.1002/cbic.201600063
Reference
4  [PMID:28029240]
  Authors
Christenson JK, Richman JE, Jensen MR, Neufeld JY, Wilmot CM, Wackett LP
  Title
beta-Lactone Synthetase Found in the Olefin Biosynthesis Pathway.
  Journal
Biochemistry 56:348-351 (2017)
DOI:10.1021/acs.biochem.6b01199
Other DBs
ExplorEnz - The Enzyme Database: 6.1.3.1
IUBMB Enzyme Nomenclature: 6.1.3.1
ExPASy - ENZYME nomenclature database: 6.1.3.1
BRENDA, the Enzyme Database: 6.1.3.1

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