KEGG   ENZYME: 2.3.1.260
Entry
EC 2.3.1.260                Enzyme                                 
Name
tetracycline polyketide synthase
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
Sysname
malonyl-CoA:malonamoyl-[OxyC acyl-carrier protein] malonyltransferase
Reaction(IUBMB)
malonamoyl-[OxyC acyl-carrier protein] + 8 malonyl-CoA = 18-carbamoyl-3,5,7,9,11,13,15,17-octaoxooctadecanoyl-[OxyC acyl-carrier protein] + 8 CO2 + 8 CoA [RN:R11516]
Reaction(KEGG)
R11516
Substrate
malonamoyl-[OxyC acyl-carrier protein];
malonyl-CoA [CPD:C00083]
Product
18-carbamoyl-3,5,7,9,11,13,15,17-octaoxooctadecanoyl-[OxyC acyl-carrier protein];
CO2 [CPD:C00011];
CoA [CPD:C00010]
Comment
The synthesis, in the bacterium Streptomyces rimosus, of the tetracycline antibiotics core skeleton requires a minimal polyketide synthase (PKS) consisting of a ketosynthase (KS), a chain length factor (CLF), and an acyl-carrier protein (ACP). Initiation involves an amide-containing starter unit that becomes the C-2 amide that is present in the tetracycline compounds. Following the initiation, the PKS catalyses the iterative condensation of 8 malonyl-CoA molecules to yield the polyketide backbone of tetracycline. Throughout the proccess, the nascent chain is attached to the OxyC acyl-carrier protein.
History
EC 2.3.1.260 created 2016
Pathway
ec00253  Tetracycline biosynthesis
ec01056  Biosynthesis of type II polyketide backbone
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K05551  minimal PKS ketosynthase (KS/KS alpha)
K05552  minimal PKS chain-length factor (CLF/KS beta)
Genes
MBDMEBOL_003040 MEBOL_003041
MSAOMYCSP_12695 MYCSP_12700
MSALDSM43276_02542 DSM43276_02543
NBRO3I_007445 O3I_007450 O3I_015110 O3I_015115
NNONONO_c10800 NONO_c10810
NTPCRH09_08670 CRH09_08675
NOZDMB37_03465 DMB37_03470
NAHF5544_10730 F5544_10735 F5544_17020 F5544_17025 F5544_31060 F5544_31065
NIEKV110_14170 KV110_14175
NTCKHQ06_30030 KHQ06_30035
NYALTV02_09610 LTV02_09615
NGPLTT66_26670 LTT66_26675
SCOSCO5087(actIORF1) SCO5088(actIORF2)
SMASAVERM_2375(pks9-3) SAVERM_2376(pks9-4)
SSXSACTE_5202 SACTE_5203 SACTE_6346 SACTE_6347
SHYSHJG_1188 SHJG_1189
SHOSHJGH_1023 SHJGH_1024
SFASfla_5317 Sfla_5318
SBHSBI_06844 SBI_06845
SVESVEN_5977 SVEN_5981
SDVBN159_2470 BN159_2471 BN159_2514(tcmL) BN159_2515(tcmK)
SALSSLNWT_5121 SLNWT_5122
STRPF750_1305(whiE-KS) F750_1306(whiE-CLF)
SFISFUL_4002 SFUL_4003
SCIB446_13320 B446_13325
SALUDC74_6590 DC74_6591
SALLSAZ_34270 SAZ_34275
SLVSLIV_12945 SLIV_12950
SGUSGLAU_26355(tcmK) SGLAU_26360(tcmL) SGLAU_28975 SGLAU_28980
SVTSVTN_18775 SVTN_18780 SVTN_28595 SVTN_28600
STREGZL_p00214 GZL_p00215
SCWTU94_31825 TU94_31830
SLDT261_0018 T261_0019 T261_6830 T261_6831
SXISXIM_35600 SXIM_35610
STRMM444_36340
STRCAA958_14835 AA958_14840 AA958_30255 AA958_30260
SAMBSAM23877_0195(alpB) SAM23877_0196(alpA) SAM23877_0207(alpQ) SAM23877_0208(alpR) SAM23877_7465(alpR) SAM23877_7466(alpQ) SAM23877_7477(alpA) SAM23877_7478(alpB)
SPRISPRI_0266 SPRI_0267 SPRI_0278 SPRI_0280 SPRI_7073 SPRI_7075 SPRI_7086 SPRI_7087
SCZABE83_16240 ABE83_16245
SCXAS200_01090 AS200_01095
SRWTUE45_01296 TUE45_01297 TUE45_01569 TUE45_01570
STRFASR50_01170 ASR50_01175 ASR50_34265 ASR50_34270
SPAVSpa2297_32720 Spa2297_32725
SGSAVL59_46040 AVL59_46045
SGMGCM10017557_73750(fabF) GCM10017557_73760
SLSSLINC_6894 SLINC_6895
STRDNI25_18955 NI25_18960
SVUB1H20_09640 B1H20_09645
SPUNBFF78_19350 BFF78_19355
SLAUSLA_3073 SLA_3074
SALJSMD11_0675(actI1) SMD11_0676(actI2) SMD11_1144(actI2) SMD11_6044(actI1) SMD11_6045(actI2)
SLXSLAV_40240 SLAV_40245 SLAV_40510 SLAV_40515
SNZDC008_13175 DC008_13180
SGEDWG14_07359 DWG14_07360
SLKSLUN_33540 SLUN_33545
SDXC4B68_09595 C4B68_09600
SGDELQ87_00815 ELQ87_00820 ELQ87_08170 ELQ87_08175
SCYAEJ357_29965 EJ357_29970 EJ357_34775 EJ357_34780
SNQCP978_29745 CP978_29750
STIRDDW44_27775 DDW44_27780
SKACP970_02735 CP970_02740 CP970_39675 CP970_39680
SGZC0216_31850 C0216_31855
SNKCP967_10255 CP967_10260
SHAWCEB94_23570 CEB94_23575
SRKFGW37_04255 FGW37_04260 FGW37_16265 FGW37_16270
SFICEIZ62_03845 EIZ62_03850
SGALCP966_29070 CP966_29075
SSPODDQ41_07350 DDQ41_07355
SVRCP971_23915 CP971_23920
SFYGFH48_20450 GFH48_20455
SAQUEJC51_31355 EJC51_31360
SGFHEP81_07942 HEP81_07943
SCAVCVT27_18210 CVT27_18215
SRIMCP984_02375 CP984_02380
SCINCP977_28050 CP977_28055
SPACB1H29_00520 B1H29_00525 B1H29_36535 B1H29_36540
STSUB7R87_22035 B7R87_22040
SCHACP983_03645 CP983_03650 CP983_27885 CP983_27890
SGXH4W23_11745 H4W23_11750
SCOECP976_32910 CP976_32915
SBATG4Z16_23870 G4Z16_23875
SSPBCP982_19000 CP982_19005
SNFJYK04_04012 JYK04_04013
SPLACP981_11515 CP981_11520 CP981_34525 CP981_34530
STUIGCM10017668_38110(fabF) GCM10017668_38120
SCHFIPT68_15425 IPT68_15430
SHUNDWB77_05172 DWB77_05173
SHARHUT13_24890 HUT13_24895
SCYGS1361_29855 S1361_29860
SFEUIM697_37550 IM697_37555
SLIAHA039_05715 HA039_05720
SDWK7C20_32760 K7C20_32765
SCALI6J39_09855 I6J39_09860
SAUHSU9_027635 SU9_027640
SMOBJ7W19_30835 J7W19_30840
SPEUCGZ69_24310 CGZ69_24315
SROIIAG44_01160 IAG44_09610 IAG44_09615 IAG44_37955 IAG44_37960 IAG44_41430 IAG44_41435
SXNIAG42_35940 IAG42_35945 IAG42_36715 IAG42_36720
SHKJ2N69_28355 J2N69_28360
SANUK7396_04305 K7396_04310
SDDD9753_08525 D9753_08530
SACTDMT42_11840 DMT42_11845
SMAOCAG99_12130 CAG99_12135
SGOBtest1122_15630 test1122_15635
SINEKI385_25170 KI385_25175
SLFJEQ17_32810 JEQ17_32815
SDECL3078_20575 L3078_20580
KABB7C62_31265 B7C62_31270
KAUB6264_18490 B6264_18495
KITCFP65_4148 CFP65_4149
YIALO772_34315 LO772_34320
LMOIVV02_05815 VV02_05820
TFUTfu_1218 Tfu_1219
TALXFOF52_07540 FOF52_07545
TCUTcur_2772 Tcur_2773
AGRAAGRA3207_002370 AGRA3207_002371
SROSros_4150 Sros_4151
NOABKM31_22830 BKM31_22870
NCXNocox_12685 Nocox_12790
FRAFrancci3_4100 Francci3_4101 Francci3_4148
FRIFraEuI1c_1317 FraEuI1c_1318
SVISvir_33690 Svir_33700
AMDAMED_5434(fabF) AMED_5435(fabF)
AMNRAM_27700 RAM_27705
AMMAMES_5369(fabF) AMES_5370(fabF)
AMZB737_5369(fabF) B737_5370(fabF)
AORISD37_09325 SD37_09330 SD37_34200 SD37_34300
APRTMUY14_22560 MUY14_22565
PSEQAD006_30015 AD006_30020
PECQAD017_31230 AD017_31235
PHHAFB00_31125 AFB00_31130
SESPBN6_54860 BN6_54870
SSYIEKG83_16315 EKG83_16320 EKG83_32215 EKG83_32220
KALKALB_7830 KALB_7831
KPHYAOZ06_32110 AOZ06_32115
LEDBBK82_02450 BBK82_02455
AHMTL08_10465 TL08_10470
ACTIUA75_11090 UA75_11095
ACADUA74_11000 UA74_11005
AHGAHOG_10345 AHOG_10350
ACTAC1701_02395 C1701_02400
ALOCRK55091 CRK55092
PMADBAY61_07805 BAY61_07810
ACTUActkin_02486 Actkin_02487
STPStrop_2223 Strop_2224
MAUMicau_4018 Micau_4019
MILML5_4402 ML5_4403
MICHFJK98_03840 FJK98_03845
MSAGGCM10017556_44980 GCM10017556_44990(fabF)
VMAVAB18032_18170 VAB18032_18175
AMSAMIS_50420 AMIS_50430 AMIS_50640 AMIS_50650
ACTNL083_3108 L083_3109
AIHAiant_86560(fabF_2) Aiant_86570(fabF_3)
ACTRAsp14428_76450(fabF_2) Asp14428_76460(fabF_3)
PLKCIK06_11005 CIK06_11010
VERHUT12_05335 HUT12_05340
CATICS0771_73180(fabF_1) CS0771_73190
DVCDvina_17880 Dvina_17885
NHYJQS43_06230 JQS43_06235
CCAZCOUCH_16055 COUCH_16060
CAICaci_3546 Caci_3547 Caci_6485 Caci_6486
 » show all
Reference
1
  Authors
Thomas, R. and Williams, D.J.
  Title
Oxytetracycline biosynthesis: origin of the carboxamide substituent.
  Journal
J Chem Soc, Chem Commun 677-679 (1983)
Reference
2  [PMID:16597959]
  Authors
Zhang W, Ames BD, Tsai SC, Tang Y
  Title
Engineered biosynthesis of a novel amidated polyketide, using the malonamyl-specific initiation module from the oxytetracycline polyketide synthase.
  Journal
Appl Environ Microbiol 72:2573-80 (2006)
DOI:10.1128/AEM.72.4.2573-2580.2006
  Sequence
Reference
3  [PMID:22500899]
  Authors
Yu L, Cao N, Wang L, Xiao C, Guo M, Chu J, Zhuang Y, Zhang S
  Title
Oxytetracycline biosynthesis improvement in Streptomyces rimosus following duplication of minimal PKS genes.
  Journal
Enzyme Microb Technol 50:318-24 (2012)
DOI:10.1016/j.enzmictec.2012.03.001
Other DBs
ExplorEnz - The Enzyme Database: 2.3.1.260
IUBMB Enzyme Nomenclature: 2.3.1.260
ExPASy - ENZYME nomenclature database: 2.3.1.260
BRENDA, the Enzyme Database: 2.3.1.260
LinkDB

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