KEGG   ENZYME: 2.3.1.292
Entry
EC 2.3.1.292                Enzyme                                 

Name
(phenol)carboxyphthiodiolenone synthase;
ppsABCDE (gene names)
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
Sysname
(methyl)malonyl-CoA:long-chain acyl-[(phenol)carboxyphthiodiolenone synthase] (methyl)malonyltransferase {carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase]-forming}
Reaction(IUBMB)
(1) 3 malonyl-CoA + 2 (S)-methylmalonyl-CoA + icosanoyl-[(phenol)carboxyphthiodiolenone synthase] + 5 NADPH = C32-carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase] + 5 CoA + 5 NADP+ + 5 CO2 + 2 H2O;
(2) 3 malonyl-CoA + 2 (S)-methylmalonyl-CoA + docosanoyl-[(phenol)carboxyphthiodiolenone synthase] + 5 NADPH = C34-carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase] + 5 CoA + 5 NADP+ + 5 CO2 + 2 H2O;
(3) 3 malonyl-CoA + 2 (S)-methylmalonyl-CoA + 19-(4-hydroxyphenyl)-nonadecanoyl-[(phenol)carboxyphthiodiolenone synthase] + 5 NADPH = C37-(phenol)carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase] + 5 CoA + 5 NADP+ + 5 CO2 + 2 H2O;
(4) 3 malonyl-CoA + 2 (S)-methylmalonyl-CoA + 17-(4-hydroxyphenyl)heptadecanoyl-[(phenol)carboxyphthiodiolenone synthase] + 5 NADPH = C35-(phenol)carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase] + 5 CoA + 5 NADP+ + 5 CO2 + 2 H2O
Substrate
malonyl-CoA [CPD:C00083];
(S)-methylmalonyl-CoA [CPD:C00683];
icosanoyl-[(phenol)carboxyphthiodiolenone synthase] [CPD:C22226];
NADPH [CPD:C00005];
docosanoyl-[(phenol)carboxyphthiodiolenone synthase];
19-(4-hydroxyphenyl)-nonadecanoyl-[(phenol)carboxyphthiodiolenone synthase];
17-(4-hydroxyphenyl)heptadecanoyl-[(phenol)carboxyphthiodiolenone synthase]
Product
C32-carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase];
CoA [CPD:C00010];
NADP+ [CPD:C00006];
CO2 [CPD:C00011];
H2O [CPD:C00001];
C34-carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase];
C37-(phenol)carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase];
C35-(phenol)carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone synthase]
Comment
The enzyme, which is a complex of five polyketide synthase proteins, is involved in the synthesis of the lipid core common to phthiocerols and phenolphthiocerols. The first protein, PpsA, can accept either a C18 or C20 long-chain fatty acyl, or a (4-hydroxyphenyl)-C17 or C19 fatty acyl. The substrates must first be adenylated by EC 6.2.1.59, long-chain fatty acid adenylase/transferase FadD26, which also loads them onto PpsA. PpsA then extends them using a malonyl-CoA extender unit. The PpsB protein adds the next malonyl-CoA extender unit. The absence of a dehydratase and an enoyl reductase domains in the PpsA and PpsB modules results in the formation of the diol portion of the phthiocerol moiety. PpsC adds a third malonyl unit (releasing a water molecule due to its dehydratase domain), PpsD adds an (R)-methylmalonyl unit, releasing a water molecule, and PpsE adds a second (R)-methylmalonyl unit, without releasing a water molecule. The incorporation of the methylmalonyl units results in formation of two branched methyl groups in the elongated product. The enzyme does not contain a thioesterase domain [2], and release of the products requires the tesA-encoded type II thioesterase [1].
History
EC 2.3.1.292 created 2019
Orthology
K12440  phthiocerol/phenolphthiocerol synthesis type-I polyketide synthase A
K12441  phthiocerol/phenolphthiocerol synthesis type-I polyketide synthase B
K12442  phthiocerol/phenolphthiocerol synthesis type-I polyketide synthase C
K12443  phthiocerol/phenolphthiocerol synthesis type-I polyketide synthase D
K12444  phthiocerol/phenolphthiocerol synthesis type-I polyketide synthase E
Genes
ECP: ECP_1966 ECP_1972 ECP_1978
ECI: UTI89_C2209 UTI89_C2215 UTI89_C2221
EIH: ECOK1_2172 ECOK1_2178 ECOK1_2184
ECC: c2453 c2460 c2468
EAB: ECABU_c22660 ECABU_c22720 ECABU_c22790
ELU: UM146_07100 UM146_07135 UM146_07165
ELC: i14_2263 i14_2270 i14_2277
ELD: i02_2263 i02_2270 i02_2277
ECOI: ECOPMV1_02095(ppsE_2) ECOPMV1_02101(ppsE_3) ECOPMV1_02107(ppsE_4)
KPP: A79E_1664(clbC) A79E_1670(clbI) A79E_1676(clbO)
KPNK: BN49_3616(clbO) BN49_3621(clbI) BN49_3627(clbC)
EAY: EAM_2973
XBV: XBW1_1403(xcnL)
XNE: XNC1_1700(xcnL)
XNM: XNC2_1650(xcnL)
XDO: XDD1_1802(xcnL)
LEM: LEN_2605
VTA: B0238
PEN: PSEEN2153
PSEN: PNC201_00715(ppsE1) PNC201_00720(ppsE2) PNC201_03625(ppsE3)
TMC: LMI_0663
MMAI: sS8_1940
HCH: HCH_03484
HEL: HELO_2407A(wcbR)
HAM: HALO3175
RSY: RSUY_35380(ppsA_2)
RPI: Rpic_1146
BTD: BTI_5243
BOK: DM82_2460
BOC: BG90_2274
BVE: AK36_5675
BAM: Bamb_6477
BCT: GEM_2743
BCON: NL30_34415
BUB: BW23_5767
BTEI: WS51_14210
BGU: KS03_4642
BUK: MYA_5597
BUL: BW21_4865
BPA: BPP2950(wcbR)
BBR: BB2918(wcbR)
BBX: BBS798_2747(wcbR)
BHM: D558_0637
BHZ: ACR54_03904(eryA)
BTRM: SAMEA390648700501(wcbR)
AAV: Aave_3732
AAA: Acav_3649
DAC: Daci_4755
BBAG: E1O_12990
NEU: NE1389(rkpA)
SPLB: SFPGR_22300(wcbR)
SNIV: SFSGTM_14590(wcbR)
AZA: AZKH_0255(rkpA_wcbR)
DDS: Ddes_1336
CCX: COCOR_02058(ppsE) COCOR_02573(ppsE1) COCOR_04217(ppsE3) COCOR_04395(ppsE4) COCOR_05109(chiB) COCOR_05739(ppsE7)
SCL: sce8261
RTR: RTCIAT899_CH06840(rkpA)
XAU: Xaut_3805
SNO: Snov_1759
MDI: METDI2708
MEX: Mext_1947
MCH: Mchl_2223
MPO: Mpop_1838
MET: M446_0317
MNO: Mnod_1945
MOR: MOC_1166
META: Y590_09055
MSL: Msil_2723
MSC: BN69_1426
MMED: Mame_04385(pksM)
BQY: MUS_3858(bacC)
BAMF: U722_01285
BWW: bwei_3106
BPUS: UP12_03550
BJS: MY9_0753
BEO: BEH_10700
CBEI: LF65_04136
CKL: CKL_1731
CKR: CKR_1605
CSR: Cspa_c03870(ppsE)
CCE: Ccel_2330
CCEL: CCDG5_0917
VRM: 44547418_00108(pksJ)
PFT: JBW_00054
MANA: MAMMFC1_04123(pksL_4) MAMMFC1_04172(pksL_7)
MTU: Rv2931(ppsA) Rv2932(ppsB) Rv2933(ppsC) Rv2934(ppsD) Rv2935(ppsE)
MRA: MRA_2957(ppsA) MRA_2958(ppsB) MRA_2959(ppsC) MRA_2960(ppsD) MRA_2961(ppsE)
MTUR: CFBS_3089(ppsA) CFBS_3090(ppsB) CFBS_3091(ppsC) CFBS_3092(ppsD) CFBS_3093(ppsE)
MTO: MTCTRI2_2988(ppsA) MTCTRI2_2989(ppsB) MTCTRI2_2990(ppsC) MTCTRI2_2991(ppsD) MTCTRI2_2992(ppsE)
MTD: UDA_2931(ppsA) UDA_2932(ppsB) UDA_2933(ppsC) UDA_2934(ppsD) UDA_2935(ppsE)
MTUT: HKBT1_3077(ppsA) HKBT1_3078(ppsB) HKBT1_3079(ppsC) HKBT1_3080(ppsD) HKBT1_3081(ppsE)
MTUU: HKBT2_3082(ppsA) HKBT2_3083(ppsB) HKBT2_3084(ppsC) HKBT2_3085(ppsD) HKBT2_3086(ppsE)
MTQ: HKBS1_3084(ppsA) HKBS1_3085(ppsB) HKBS1_3086(ppsC) HKBS1_3087(ppsD) HKBS1_3088(ppsE)
MBB: BCG_2953(ppsA) BCG_2954(ppsB) BCG_2955(ppsC) BCG_2956(ppsD) BCG_2957(ppsE)
MBT: JTY_2948(ppsA) JTY_2949(ppsB) JTY_2950(ppsC) JTY_2951(ppsD) JTY_2952(ppsE)
MBM: BCGMEX_2948(ppsA) BCGMEX_2949(ppsB) BCGMEX_2950(ppsC) BCGMEX_2951(ppsD) BCGMEX_2952(ppsE)
MAF: MAF_29360(ppsA) MAF_29370(ppsB) MAF_29380(ppsC) MAF_29390(ppsD) MAF_29400(ppsE)
MCE: MCAN_29531(ppsA) MCAN_29541(ppsB) MCAN_29551(ppsC) MCAN_29561(ppsD) MCAN_29571(ppsE)
MCQ: BN44_60408(ppsA) BN44_60409(ppsB) BN44_60410(ppsC) BN44_60411(ppsD) BN44_60412(ppsE)
MCV: BN43_40639(ppsA) BN43_40640(ppsB) BN43_40641(ppsC) BN43_40642(ppsD) BN43_40643(ppsE)
MCX: BN42_40929(ppsA) BN42_40930(ppsB) BN42_40931(ppsC) BN42_40932(ppsD) BN42_40933(ppsE)
MCZ: BN45_51343(ppsA) BN45_51344(ppsB) BN45_51345(ppsC) BN45_51346(ppsD) BN45_51347(ppsE)
MUL: MUL_2015(ppsE) MUL_2016(ppsD) MUL_2017(ppsC) MUL_2018(ppsB) MUL_2019(ppsA)
MMI: MMAR_1772(ppsE) MMAR_1773(ppsD) MMAR_1774(ppsC) MMAR_1775(ppsB) MMAR_1776(ppsA)
MLI: MULP_01928(ppsE) MULP_01929(ppsD) MULP_01931(ppsC) MULP_01932(ppsB) MULP_01933(ppsA)
MSHG: MSG_01627(ppsE) MSG_01628 MSG_01629(ppsC) MSG_01630(ppsB)
MFJ: MFLOJ_16760(ppsB) MFLOJ_16770(ppsC) MFLOJ_16780(ppsD) MFLOJ_16790(ppsE)
MDU: MDUV_13110(ppsE) MDUV_13120(ppsD) MDUV_13130(ppsB_1) MDUV_13140(ppsB_2) MDUV_13160
MTER: 4434518_02133(ppsE) 4434518_02134(ppsD_1) 4434518_02135(ppsD_2) 4434518_02136(ppsA_2) 4434518_02137(ppsA_3)
MMIN: MMIN_38080(ppsE) MMIN_38090(ppsD) MMIN_38100 MMIN_38110(ppsB) MMIN_38120(ppsA)
NFA: NFA_55930
NFR: ERS450000_02790(ppsC_2) ERS450000_04268(eryA_3)
RFA: A3L23_02930(mas)
SALB: XNR_5890
SHY: SHJG_1264
STRP: F750_3218
SRW: TUE45_05028(ppsE_3)
SALJ: SMD11_6960
TCU: Tcur_4756
SRO: Sros_8815
SEN: SACE_2595
SACC: EYD13_10100(pksJ) EYD13_10110(pksL3)
AMD: AMED_3368
AMN: RAM_17125
AMM: AMES_3329
AMZ: B737_3329
AOI: AORI_3262 AORI_3406(ppsD)
AMYY: YIM_17205(ppsE) YIM_33630(ppsA4) YIM_42700(ppsA7)
SESP: BN6_35390(pks5) BN6_47930(pks10) BN6_56590(pks14)
KAL: KALB_3306
ACTI: UA75_06495
ACAD: UA74_06495
AHG: AHOG_06265(ppsE)
ACTN: L083_1487
CAI: Caci_6994
MAR: MAE_27800
MPK: VL20_5149
GLJ: GKIL_1829(ppsE)
CALH: IJ00_10275
RUL: UC8_19280(ppsC_1) UC8_19300(ppsC_2)
FLM: MY04_0042
NDO: DDD_0162(jamP)
KAN: IMCC3317_07530(ppsE_1) IMCC3317_07570(ppsE_2) IMCC3317_07950(ppsE_3) IMCC3317_08000(ppsE_4) IMCC3317_14600(pksJ)
NDE: NIDE2152
NJA: NSJP_3908
 » show all
Reference
1  [PMID:15668773]
  Authors
Rao A, Ranganathan A
  Title
Interaction studies on proteins encoded by the phthiocerol dimycocerosate locus of Mycobacterium tuberculosis.
  Journal
Mol Genet Genomics 272:571-9 (2004)
DOI:10.1007/s00438-004-1088-3
Reference
2  [PMID:15749014]
  Authors
Trivedi OA, Arora P, Vats A, Ansari MZ, Tickoo R, Sridharan V, Mohanty D, Gokhale RS
  Title
Dissecting the mechanism and assembly of a complex virulence mycobacterial lipid.
  Journal
Mol Cell 17:631-43 (2005)
DOI:10.1016/j.molcel.2005.02.009
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 2.3.1.292
IUBMB Enzyme Nomenclature: 2.3.1.292
ExPASy - ENZYME nomenclature database: 2.3.1.292
BRENDA, the Enzyme Database: 2.3.1.292

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