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
MTURv2931(ppsA) Rv2932(ppsB) Rv2933(ppsC) Rv2934(ppsD) Rv2935(ppsE)
MTVRVBD_2931 RVBD_2932 RVBD_2933 RVBD_2934 RVBD_2935
MTCMT3000 MT3002 MT3003 MT3004 MT3005
MRAMRA_2957(ppsA) MRA_2958(ppsB) MRA_2959(ppsC) MRA_2960(ppsD) MRA_2961(ppsE)
MTFTBFG_12945 TBFG_12946 TBFG_12947 TBFG_12948 TBFG_12949
MTBTBMG_01037 TBMG_01038 TBMG_01039 TBMG_01040 TBMG_01041
MTKTBSG_01045 TBSG_01046 TBSG_01047 TBSG_01048 TBSG_01049
MTZTBXG_001025 TBXG_001026 TBXG_001027 TBXG_001028 TBXG_001029
MTGMRGA327_18005 MRGA327_18040
MTIMRGA423_18145 MRGA423_18200
MTECCDC5079_2690 CCDC5079_2691 CCDC5079_2692 CCDC5079_2693 CCDC5079_2694 CCDC5079_2695
MTURCFBS_3089(ppsA) CFBS_3090(ppsB) CFBS_3091(ppsC) CFBS_3092(ppsD) CFBS_3093(ppsE)
MTLCCDC5180_2655 CCDC5180_2656 CCDC5180_2657 CCDC5180_2658 CCDC5180_2659
MTOMTCTRI2_2988(ppsA) MTCTRI2_2989(ppsB) MTCTRI2_2990(ppsC) MTCTRI2_2991(ppsD) MTCTRI2_2992(ppsE)
MTDUDA_2931(ppsA) UDA_2932(ppsB) UDA_2933(ppsC) UDA_2934(ppsD) UDA_2935(ppsE)
MTNERDMAN_3212 ERDMAN_3214(ppsB) ERDMAN_3215(ppsC) ERDMAN_3216(ppsD) ERDMAN_3217(ppsE)
MTJJ112_15685 J112_15690 J112_15695 J112_15700 J112_15705 J112_15710
MTUBMT7199_2965 MT7199_2966(ppsB) MT7199_2967 MT7199_2968 MT7199_2969
MTUCJ113_20330 J113_20385 J113_20410
MTUEJ114_15645 J114_15650 J114_15655 J114_15670 J114_15675
MTXM943_15125 M943_15130 M943_15135
MTULTBHG_02860 TBHG_02861 TBHG_02862 TBHG_02865 TBHG_04117
MTUTHKBT1_3077(ppsA) HKBT1_3078(ppsB) HKBT1_3079(ppsC) HKBT1_3080(ppsD) HKBT1_3081(ppsE)
MTUUHKBT2_3082(ppsA) HKBT2_3083(ppsB) HKBT2_3084(ppsC) HKBT2_3085(ppsD) HKBT2_3086(ppsE)
MTQHKBS1_3084(ppsA) HKBS1_3085(ppsB) HKBS1_3086(ppsC) HKBS1_3087(ppsD) HKBS1_3088(ppsE)
MBOBQ2027_MB2956(ppsA) BQ2027_MB2957(ppsB) BQ2027_MB2958(ppsC) BQ2027_MB2959(ppsD) BQ2027_MB2960(ppsE)
MBBBCG_2953(ppsA) BCG_2954(ppsB) BCG_2955(ppsC) BCG_2956(ppsD) BCG_2957(ppsE)
MBTJTY_2948(ppsA) JTY_2949(ppsB) JTY_2950(ppsC) JTY_2951(ppsD) JTY_2952(ppsE)
MBMBCGMEX_2948(ppsA) BCGMEX_2949(ppsB) BCGMEX_2950(ppsC) BCGMEX_2951(ppsD) BCGMEX_2952(ppsE)
MBKK60_030360 K60_030370 K60_030380 K60_030390 K60_030400
MBXBCGT_2769 BCGT_2770 BCGT_2771 BCGT_2772 BCGT_2773
MAFMAF_29360(ppsA) MAF_29370(ppsB) MAF_29380(ppsC) MAF_29390(ppsD) MAF_29400(ppsE)
MMICRN08_3228 RN08_3230 RN08_3232 RN08_3233 RN08_3234
MCEMCAN_29531(ppsA) MCAN_29541(ppsB) MCAN_29551(ppsC) MCAN_29561(ppsD) MCAN_29571(ppsE)
MCQBN44_60408(ppsA) BN44_60409(ppsB) BN44_60410(ppsC) BN44_60411(ppsD) BN44_60412(ppsE)
MCVBN43_40639(ppsA) BN43_40640(ppsB) BN43_40641(ppsC) BN43_40642(ppsD) BN43_40643(ppsE)
MCXBN42_40929(ppsA) BN42_40930(ppsB) BN42_40931(ppsC) BN42_40932(ppsD) BN42_40933(ppsE)
MCZBN45_51343(ppsA) BN45_51344(ppsB) BN45_51345(ppsC) BN45_51346(ppsD) BN45_51347(ppsE)
MORYMO_003064(ppsB) MO_003065(ppsC) MO_003066(ppsD) MO_003067(ppsE)
MLEML2353 ML2354 ML2355 ML2356 ML2357
MLBMLBr02353 MLBr02354 MLBr02355 MLBr02356 MLBr02357
MSAMycsm_05875 Mycsm_05876 Mycsm_05877 Mycsm_05878
MULMUL_2015(ppsE) MUL_2016(ppsD) MUL_2017(ppsC) MUL_2018(ppsB) MUL_2019(ppsA)
MMIMMAR_1772(ppsE) MMAR_1773(ppsD) MMAR_1774(ppsC) MMAR_1775(ppsB) MMAR_1776(ppsA)
MMAEMMARE11_16920(ppsE) MMARE11_16930(ppsD) MMARE11_16940(ppsC) MMARE11_16960(ppsA)
MLIMULP_01928(ppsE) MULP_01929(ppsD) MULP_01931(ppsC) MULP_01932(ppsB) MULP_01933(ppsA)
MPSEMPSD_40560 MPSD_40600(ppsC) MPSD_40610(ppsD) MPSD_40620(ppsE)
MSHOMSHO_54640 MSHO_54650(ppsB) MSHO_54660(ppsC) MSHO_54670(ppsD) MSHO_54680(ppsE)
MMCMmcs_2832 Mmcs_2833 Mmcs_2834 Mmcs_2835
MKMMkms_2876 Mkms_2877 Mkms_2878 Mkms_2879
MJLMjls_2861 Mjls_2865 Mjls_2866
MKNMKAN_08430 MKAN_24020 MKAN_24025 MKAN_24030 MKAN_24035 MKAN_24040
MHADB586_03495 B586_03500 B586_03505 B586_03510 B586_03515
MDXBTO20_18125 BTO20_18130 BTO20_18135 BTO20_18140
MSHGMSG_01627(ppsE) MSG_01628 MSG_01629(ppsC) MSG_01630(ppsB)
MFJMFLOJ_16760(ppsB) MFLOJ_16770(ppsC) MFLOJ_16780(ppsD) MFLOJ_16790(ppsE)
MSTOMSTO_18320(ppsB) MSTO_18350 MSTO_18360 MSTO_18380(ppsE)
MSIMMSIM_07720 MSIM_07730 MSIM_07750(ppsC) MSIM_07760(ppsD) MSIM_07770(ppsE)
MLWMJO58_08810 MJO58_08815 MJO58_08820 MJO58_08825
MPAGC0J29_10310 C0J29_10315 C0J29_10320 C0J29_10325 C0J29_10330
MNMMNVM_38360(ppsA_2) MNVM_38370(ppsB) MNVM_38380 MNVM_38390 MNVM_38400 MNVM_38410(ppsE)
MCOOMCOO_18270(ppsE) MCOO_18280(ppsD) MCOO_18290 MCOO_18300(ppsB) MCOO_18310(ppsA_1)
MBAIMB901379_01589(ppsE_1) MB901379_01590(ppsC_2) MB901379_01591(ppsC_3) MB901379_01592(ppsB) MB901379_01593(ppsA_1)
MGAUMGALJ_49400(ppsB) MGALJ_49410(ppsE)
MLJMLAC_28670(ppsA) MLAC_28680(ppsB) MLAC_28690(ppsC) MLAC_28700(ppsD) MLAC_28710(ppsE)
MSHJMSHI_07320(ppsE) MSHI_07330(ppsD) MSHI_07340(ppsC) MSHI_07350(ppsB)
MMAMK3U93_07825 K3U93_07830 K3U93_07835 K3U93_07840 K3U93_07845
MSPGF6B93_07145 F6B93_07150 F6B93_07155 F6B93_07160 F6B93_07165
MOTLTS72_15930 LTS72_15935 LTS72_15940 LTS72_15945 LTS72_15950
MLMMLPF_2695(ppsE) MLPF_2696(ppsD) MLPF_2697(ppsC) MLPF_2698(ppsB) MLPF_2699(ppsA)
MPAAMKK62_06575 MKK62_06580 MKK62_06585 MKK62_06590 MKK62_06595
MMEHM5I08_15220 M5I08_15225 M5I08_15255 M5I08_15315 M5I08_15320 M5I08_15335
MWUPT015_10805 PT015_10810 PT015_10815 PT015_10820 PT015_10825
MVAMvan_3123 Mvan_3124 Mvan_3125 Mvan_3126 Mvan_3128
MGIMflv_3390 Mflv_3391 Mflv_3392 Mflv_3393 Mflv_3395
MSPMspyr1_27210 Mspyr1_27220 Mspyr1_27230 Mspyr1_27240 Mspyr1_27260
MCBMycch_2760 Mycch_2762 Mycch_2763 Mycch_2764 Mycch_2765
MVQMYVA_2946 MYVA_2948 MYVA_2950 MYVA_2951(ppsD) MYVA_2952(ppsE)
MDUMDUV_13110(ppsE) MDUV_13120(ppsD) MDUV_13130(ppsB_1) MDUV_13140(ppsB_2) MDUV_13160 MDUV_13170
MAUUNCTC10437_03018(ppsE_2) NCTC10437_03019(ppsB_2) NCTC10437_03020(ppsB_3) NCTC10437_03021(ppsB_4) NCTC10437_03023(ppsA_1)
MPSCMPSYJ_36560(ppsE) MPSYJ_36570(ppsD) MPSYJ_36580 MPSYJ_36590 MPSYJ_36610(ppsA)
MPOFMPOR_33390(ppsA_1) MPOR_33410(ppsB_1) MPOR_33420(ppsB_2) MPOR_33430(ppsD) MPOR_33440(ppsE)
MSEIMSEDJ_33320(ppsE) MSEDJ_33330(ppsD) MSEDJ_33340(ppsA_1) MSEDJ_33350
MMONEWR22_15015 EWR22_15020 EWR22_15025 EWR22_15030
MRFMJO55_13950 MJO55_13960 MJO55_13965 MJO55_13970 MJO55_13975
MKRMKOR_16500(ppsE) MKOR_16510(ppsD) MKOR_16520 MKOR_16530 MKOR_16540 MKOR_16550
MPAKMIU77_12300 MIU77_12305 MIU77_12320
MJDJDM601_2211(ppsE) JDM601_2212(ppsD) JDM601_2213(ppsD) JDM601_2214(ppsA) JDM601_2215
MTER4434518_02133(ppsE) 4434518_02134(ppsD_1) 4434518_02135(ppsD_2) 4434518_02136(ppsA_2) 4434518_02137(ppsA_3)
MMINMMIN_38080(ppsE) MMIN_38090(ppsD) MMIN_38100 MMIN_38110(ppsB) MMIN_38120(ppsA)
MHIBMHIB_16590(ppsE) MHIB_16600(ppsD) MHIB_16610 MHIB_16620(ppsB) MHIB_16640
MHERK3U94_12440 K3U94_12445 K3U94_12450 K3U94_12455 K3U94_12460
MVMMJO54_12385 MJO54_12390 MJO54_12395 MJO54_12400 MJO54_12405
GOILK459_21375 LK459_21380 LK459_21385 LK459_21390 LK459_21395
TPULTPB0596_38070(ppsE) TPB0596_38080(ppsD) TPB0596_38090(ppsB_1) TPB0596_38100(ppsB_2) TPB0596_38120
SDVBN159_2139 BN159_2140(ppsD) BN159_2141(ppsC) BN159_2142
SCYGS1361_37025(ppsC4)
SSPNLXH13_29765
SCOAQU709_01725 QU709_01730
TCUTcur_4756
ACTWF7P10_16280 F7P10_16315
AGRAAGRA3207_004336
SPIQOHA34_24830
SROSros_8815
NOABKM31_49270
NCXNocox_38805(ppsA9)
FRIFraEuI1c_4378
AMDAMED_3368
AMNRAM_17125
AMMAMES_3329
AMZB737_3329
AOIAORI_3406(ppsD)
AJAAJAP_22190
AMYBBKN51_15570
AABA4R43_35350
AMYYYIM_33630(ppsA4) YIM_42700(ppsA7)
AORISD37_17630
APRTMUY14_18650
AROONQK81_05420
ATHML1857_32555
SSYIEKG83_23210
KALKALB_3306
KBUQ4V64_17700
KPHYAOZ06_25910 AOZ06_30725
ALOCRK57469
ACTUActkin_02680(ppsA_5)
CROSN8J89_36490
AEYCDG81_08895
 » 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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