KEGG ENZYME: 2.3.1.260

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

MBD:	MEBOL_003040 MEBOL_003041

BALU:

QRY64_01340

BHUI:

LOK74_08075

PDY:	QJQ58_17940

PAUN:

MJA45_09960

BWX:	NQ550_10275

MSAO:

MYCSP_12695 MYCSP_12700

MSAL:

DSM43276_02542 DSM43276_02543

NBR:	O3I_007445 O3I_007450 O3I_015110 O3I_015115

NNO:	NONO_c10800 NONO_c10810

NTP:	CRH09_08670 CRH09_08675

NOZ:	DMB37_03465 DMB37_03470

NAH:	F5544_10730 F5544_10735 F5544_17020 F5544_17025 F5544_31060 F5544_31065

NIE:	KV110_14170 KV110_14175

NTC:	KHQ06_30030 KHQ06_30035

NYA:	LTV02_09610 LTV02_09615

NGP:	LTT66_26670 LTT66_26675

NSPU:

IFM12276_11090 IFM12276_11100

SCO:	SCO5087(actIORF1) SCO5088(actIORF2)

SMA:	SAVERM_2375(pks9-3) SAVERM_2376(pks9-4)

SFI:	SFUL_4002 SFUL_4003

SANL:

KZO11_29480 KZO11_29485 KZO11_31415

SGRF:

SGFS_016110 SGFS_016120

SCYE:

R2B67_24745 R2B67_24750

SSX:	SACTE_5202 SACTE_5203 SACTE_6346 SACTE_6347

SHY:	SHJG_1188 SHJG_1189

SHO:	SHJGH_1023 SHJGH_1024

SFA:	Sfla_5317 Sfla_5318

SBH:	SBI_06844 SBI_06845

SVE:	SVEN_5977 SVEN_5981

SDV:	BN159_2470 BN159_2471 BN159_2514(tcmL) BN159_2515(tcmK)

SALS:

SLNWT_5121 SLNWT_5122

STRP:

F750_1305(whiE-KS) F750_1306(whiE-CLF)

SCI:	B446_13320 B446_13325

SLV:	SLIV_12945 SLIV_12950

SGU:	SGLAU_26355(tcmK) SGLAU_26360(tcmL) SGLAU_28975 SGLAU_28980

SVT:	SVTN_18775 SVTN_18780 SVTN_28595 SVTN_28600

STRE:

GZL_p00214 GZL_p00215

SCW:	TU94_31825 TU94_31830

SLD:	T261_0018 T261_0019 T261_6830 T261_6831

SXI:	SXIM_35600 SXIM_35610

STRM:

M444_36340

STRC:

AA958_14835 AA958_14840 AA958_30255 AA958_30260

SAMB:

SAM23877_0195(alpB) SAM23877_0196(alpA) SAM23877_0207(alpQ) SAM23877_0208(alpR) SAM23877_7465(alpR) SAM23877_7466(alpQ) SAM23877_7477(alpA) SAM23877_7478(alpB)

SPRI:

SPRI_0266 SPRI_0267 SPRI_0278 SPRI_0280 SPRI_7073 SPRI_7075 SPRI_7086 SPRI_7087

SCZ:	ABE83_16240 ABE83_16245

SCX:	AS200_01090 AS200_01095

SRW:	TUE45_01296 TUE45_01297 TUE45_01569 TUE45_01570

STRF:

ASR50_01170 ASR50_01175 ASR50_34265 ASR50_34270

SPAV:

Spa2297_32720 Spa2297_32725

SGS:	AVL59_46040 AVL59_46045

SGM:	GCM10017557_73750(fabF) GCM10017557_73760

SPHW:

NFX46_12165 NFX46_12170 NFX46_24980 NFX46_24985

SLS:	SLINC_6894 SLINC_6895

SALU:

DC74_6590 DC74_6591

SALL:

SAZ_34270 SAZ_34275

STRD:

NI25_18955 NI25_18960

SVU:	B1H20_09640 B1H20_09645

SPUN:

BFF78_19350 BFF78_19355

SLAU:

SLA_3073 SLA_3074

SALJ:

SMD11_0675(actI1) SMD11_0676(actI2) SMD11_1144(actI2) SMD11_6044(actI1) SMD11_6045(actI2)

SLX:	SLAV_40240 SLAV_40245 SLAV_40510 SLAV_40515

SNZ:	DC008_13175 DC008_13180

SGE:	DWG14_07359 DWG14_07360

SLK:	SLUN_33540 SLUN_33545

SDX:	C4B68_09595 C4B68_09600

SGD:	ELQ87_00815 ELQ87_00820 ELQ87_08170 ELQ87_08175

SCYA:

EJ357_29965 EJ357_29970 EJ357_34775 EJ357_34780

SNQ:	CP978_29745 CP978_29750

STIR:

DDW44_27775 DDW44_27780

SKA:	CP970_02735 CP970_02740 CP970_39675 CP970_39680

SGZ:	C0216_31850 C0216_31855

SNK:	CP967_10255 CP967_10260

SHAW:

CEB94_23570 CEB94_23575

SRK:	FGW37_04255 FGW37_04260 FGW37_16265 FGW37_16270

SFIC:

EIZ62_03845 EIZ62_03850

SGAL:

CP966_29070 CP966_29075

SSPO:

DDQ41_07350 DDQ41_07355

SVR:	CP971_23915 CP971_23920

SFY:	GFH48_20450 GFH48_20455

SAQU:

EJC51_31355 EJC51_31360

SGF:	HEP81_07942 HEP81_07943

SCAV:

CVT27_18210 CVT27_18215

SRIM:

CP984_02375 CP984_02380

SCIN:

CP977_28050 CP977_28055

SPAC:

B1H29_00520 B1H29_00525 B1H29_36535 B1H29_36540

STSU:

B7R87_22035 B7R87_22040

SCHA:

CP983_03645 CP983_03650 CP983_27885 CP983_27890

SGX:	H4W23_11745 H4W23_11750

SCOE:

CP976_32910 CP976_32915

SBAT:

G4Z16_23870 G4Z16_23875

SSPB:

CP982_19000 CP982_19005

SNF:	JYK04_04012 JYK04_04013

SPLA:

CP981_11515 CP981_11520 CP981_34525 CP981_34530

STUI:

GCM10017668_38110(fabF) GCM10017668_38120

SCHF:

IPT68_15425 IPT68_15430

SHUN:

DWB77_05172 DWB77_05173

SHAR:

HUT13_24890 HUT13_24895

SCYG:

S1361_29855 S1361_29860

SFEU:

IM697_37550 IM697_37555

SLIA:

HA039_05715 HA039_05720

SDW:	K7C20_32760 K7C20_32765

SCAL:

I6J39_09855 I6J39_09860

SAUH:

SU9_027635 SU9_027640

SMOB:

J7W19_30835 J7W19_30840

SPEU:

CGZ69_24310 CGZ69_24315

SROI:

IAG44_01160 IAG44_09610 IAG44_09615 IAG44_37955 IAG44_37960 IAG44_41430 IAG44_41435

SXN:	IAG42_35940 IAG42_35945 IAG42_36715 IAG42_36720

SHK:	J2N69_28355 J2N69_28360

SANU:

K7396_04305 K7396_04310

SDD:	D9753_08525 D9753_08530

SACT:

DMT42_11840 DMT42_11845

SMAO:

CAG99_12130 CAG99_12135

SGOB:

test1122_15630 test1122_15635

SINE:

KI385_25170 KI385_25175

SLF:	JEQ17_32810 JEQ17_32815

SDEC:

L3078_20575 L3078_20580

SDUR:

M4V62_10140

SYAN:

NRK68_34875 NRK68_34880

STAA:

LDH80_09580 LDH80_09585

SNIG:

HEK616_47540 HEK616_47550(fabF_4)

SSPN:

LXH13_13940 LXH13_13945

SCIR:

STRCI_006078 STRCI_006079 STRCI_006121 STRCI_006122

SLON:

LGI35_31850 LGI35_31855

SDRZ:

NEH16_30130 NEH16_32490 NEH16_32495

STUD:

STRTU_005094 STRTU_005095

SGK:	PET44_33780

SARG:

HKX69_34105 HKX69_34110

SJN:	RI060_18275 RI060_18280

SCYN:

N8I84_12665 N8I84_12670

SOV:	QZH56_16780 QZH56_16790 QZH56_23785 QZH56_23790

SHAU:

K9S39_40675 K9S39_40680

SKG:	KJK29_16070 KJK29_16075

SLAI:

P8A22_09045

SROC:

RGF97_06495

STTN:

BSL84_24940 BSL84_24945

SINN:

ABB07_18370 ABB07_18375

KAB:	B7C62_31265 B7C62_31270

KAU:	B6264_18490 B6264_18495

KIT:	CFP65_4148 CFP65_4149

KIS:	HUT16_23685 HUT16_23690

YIA:	LO772_34315 LO772_34320

STRH:

GXP74_03140 GXP74_03145

ABRY:

NYE86_15465 NYE86_15470 NYE86_15935 NYE86_15940

AGLA:

OIE69_26820 OIE69_26825

LMOI:

VV02_05815 VV02_05820

TFU:	Tfu_1218 Tfu_1219

TALX:

FOF52_07540 FOF52_07545

NAKE:

KGD83_03910

TCU:	Tcur_2772 Tcur_2773

AGRA:

AGRA3207_002370 AGRA3207_002371

ACIR:

OG979_01950 OG979_01955 OG979_20965 OG979_20970 OG979_36250 OG979_36255

SPIQ:

OHA34_06340 OHA34_06345

SRO:	Sros_4150 Sros_4151

NOA:	BKM31_22830 BKM31_22870

NCX:	Nocox_12685 Nocox_12790

FRA:	Francci3_4100 Francci3_4101 Francci3_4148

FRI:	FraEuI1c_1317 FraEuI1c_1318

SVI:	Svir_33690 Svir_33700

AMD:	AMED_5434(fabF) AMED_5435(fabF)

AMN:	RAM_27700 RAM_27705

AMM:	AMES_5369(fabF) AMES_5370(fabF)

AMZ:	B737_5369(fabF) B737_5370(fabF)

AORI:

SD37_09325 SD37_09330 SD37_34200 SD37_34300

APRT:

MUY14_22560 MUY14_22565

PSEQ:

AD006_30015 AD006_30020

PECQ:

AD017_31230 AD017_31235

PHH:	AFB00_31125 AFB00_31130

SESP:

BN6_54860 BN6_54870

SSYI:

EKG83_16315 EKG83_16320 EKG83_32215 EKG83_32220

KAL:	KALB_7830 KALB_7831

KUT:	JJ691_15650 JJ691_15660

KBU:	Q4V64_27180 Q4V64_27185

KPHY:

AOZ06_32110 AOZ06_32115

LED:	BBK82_02450 BBK82_02455

AHM:	TL08_10465 TL08_10470

ACTI:

UA75_11090 UA75_11095

ACAD:

UA74_11000 UA74_11005

AHG:	AHOG_10345 AHOG_10350

ACTA:

C1701_02395 C1701_02400

ALO:	CRK55091 CRK55092

PMAD:

BAY61_07805 BAY61_07810

ACTU:

Actkin_02486 Actkin_02487

CROS:

N8J89_20275 N8J89_20280

STP:	Strop_2223 Strop_2224

MAU:	Micau_4018 Micau_4019

MIL:	ML5_4402 ML5_4403

MICH:

FJK98_03840 FJK98_03845

MSAG:

GCM10017556_44980 GCM10017556_44990(fabF)

VMA:	VAB18032_18170 VAB18032_18175

VER:	HUT12_05335 HUT12_05340

MENO:

Jiend_01490

MCHL:

PVK74_07695

MFEU:

H1D33_23035 H1D33_25695 H1D33_25700

MHAW:

RMN56_24400

AMS:	AMIS_50420 AMIS_50430 AMIS_50640 AMIS_50650

ACTN:

L083_3108 L083_3109

AIH:	Aiant_86560(fabF_2) Aiant_86570(fabF_3)

ACTR:

Asp14428_76450(fabF_2) Asp14428_76460(fabF_3)

ACTL:

L3i22_085310 L3i22_085320

PLK:	CIK06_11005 CIK06_11010

CATI:

CS0771_73180(fabF_1) CS0771_73190

DVC:	Dvina_17880 Dvina_17885

DFU:	Dfulv_18390 Dfulv_18395

DROS:

Drose_14695 Drose_14745 Drose_24330 Drose_24335

DAUR:

Daura_28645 Daura_28650 Daura_37850 Daura_37855

NHY:	JQS43_06230 JQS43_06235

CCAZ:

COUCH_16055 COUCH_16060

CAI:	Caci_3546 Caci_3547 Caci_6485 Caci_6486

KBB:	ccbrp13_66820(fabF_2) ccbrp13_66830

BMEI:

Spa11_38550

» show all

Reference

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

[ag:AAZ78325 AAZ78326 AAZ78327]

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

DBGET integrated database retrieval system