KEGG   ENZYME: 2.3.1.287
Entry
EC 2.3.1.287                Enzyme                                 
Name
phthioceranic/hydroxyphthioceranic acid synthase;
msl2 (gene name);
PKS2
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
Sysname
(S)-methylmalonyl-CoA:palmitoyl-[(hydroxy)phthioceranic acid synthase] methylmalonyltransferase (phthioceranyl-[(hydroxy)phthioceranic acid synthase]-forming)
Reaction(IUBMB)
(1) 8 (S)-methylmalonyl-CoA + palmitoyl-[(hydroxy)phthioceranic acid synthase] + 16 NADPH + 16 H+ = 8 CoA + C40-phthioceranyl-[(hydroxy)phthioceranic acid synthase] + 16 NADP+ + 8 CO2 + 8 H2O [RN:R12380];
(2) 7 (S)-methylmalonyl-CoA + palmitoyl-[(hydroxy)phthioceranic acid synthase] + 14 NADPH + 14 H+ = 7 CO2 + C37-phthioceranyl-[(hydroxy)phthioceranic acid synthase] + 14 NADP+ + 7 CoA + 7 H2O [RN:R12381]
Reaction(KEGG)
R12380 R12381
Substrate
(S)-methylmalonyl-CoA [CPD:C00683];
palmitoyl-[(hydroxy)phthioceranic acid synthase] [CPD:C22124];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Product
CoA [CPD:C00010];
C40-phthioceranyl-[(hydroxy)phthioceranic acid synthase] [CPD:C22125];
NADP+ [CPD:C00006];
CO2 [CPD:C00011];
H2O [CPD:C00001];
C37-phthioceranyl-[(hydroxy)phthioceranic acid synthase] [CPD:C22126]
Comment
This mycobacterial polyketide enzyme produces the hepta- and octa-methylated fatty acids known as phthioceranic acids, and presumably their hydroxylated versions. Formation of hepta- and octamethylated products depends on whether the enzyme incorporates seven or eight methylmalonyl-CoA extender units, respectively. Formation of hydroxylated products may result from the enzyme skipping the dehydratase (DH) and enoylreductase (ER) domains during the first cycle of condensation [2].
History
EC 2.3.1.287 created 2019
Orthology
K12431  phthioceranic/hydroxyphthioceranic acid synthase
Genes
BOB: GN304_08335
BOMB: GT348_07885
MTU: Rv3825c(pks2)
MTV: RVBD_3825c
MTC: MT3933(mas-3)
MRA: MRA_3865(pks2)
MTF: TBFG_13859
MTB: TBMG_03872
MTK: TBSG_03895
MTZ: TBXG_003842
MTE: CCDC5079_3555
MTUR: CFBS_4055
MTL: CCDC5180_3504
MTO: MTCTRI2_3904(pks2)
MTD: UDA_3825c(pks2)
MTN: ERDMAN_4192(pks2)
MTJ: J112_20565
MTUB: MT7199_3894
MTUE: J114_20440
MTX: M943_19640
MTUH: I917_26895
MTUL: TBHG_03763
MTUT: HKBT1_4038(pks2)
MTUU: HKBT2_4048(pks2)
MTQ: HKBS1_4051(pks2)
MBO: BQ2027_MB3855C(pks2)
MBB: BCG_3888c(pks2)
MBT: JTY_3890(pks2)
MBM: BCGMEX_3889c(pks2)
MBK: K60_039690
MBX: BCGT_3690
MAF: MAF_38400(pks2)
MMIC: RN08_4223
MCE: MCAN_38441(pks2)
MCQ: BN44_120235(pks)
MCV: BN43_90342(pks)
MCX: BN42_90353(pks)
MCZ: BN45_110187(pks)
MORY: MO_003977(pks2)
MPA: MAP_3764c(pks2)
MBAI: MB901379_03143(pks2_3)
MGAU: MGALJ_24090(pks2)
NBR: O3I_032485
AEY: CDG81_17105
 » show all
Reference
1  [PMID:11278910]
  Authors
Sirakova TD, Thirumala AK, Dubey VS, Sprecher H, Kolattukudy PE
  Title
The Mycobacterium tuberculosis pks2 gene encodes the synthase for the hepta- and octamethyl-branched fatty acids required for sulfolipid synthesis.
  Journal
J Biol Chem 276:16833-9 (2001)
DOI:10.1074/jbc.M011468200
  Sequence
[mtu:Rv3825c]
Reference
2  [PMID:17389997]
  Authors
Gokhale RS, Saxena P, Chopra T, Mohanty D
  Title
Versatile polyketide enzymatic machinery for the biosynthesis of complex mycobacterial lipids.
  Journal
Nat Prod Rep 24:267-77 (2007)
DOI:10.1039/b616817p
Reference
3  [PMID:24028583]
  Authors
Passemar C, Arbues A, Malaga W, Mercier I, Moreau F, Lepourry L, Neyrolles O, Guilhot C, Astarie-Dequeker C
  Title
Multiple deletions in the polyketide synthase gene repertoire of Mycobacterium tuberculosis reveal functional overlap of cell envelope lipids in host-pathogen interactions.
  Journal
Cell Microbiol 16:195-213 (2014)
DOI:10.1111/cmi.12214
  Sequence
[mtu:Rv3825c]
Other DBs
ExplorEnz - The Enzyme Database: 2.3.1.287
IUBMB Enzyme Nomenclature: 2.3.1.287
ExPASy - ENZYME nomenclature database: 2.3.1.287
BRENDA, the Enzyme Database: 2.3.1.287

  All links  
Chemical substance (10)   
   KEGG COMPOUND (10)   
Chemical reaction (2)   
   KEGG REACTION (2)   
Gene (45)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (44)   
Protein sequence (10)   
   UniProt (5)   
   SWISS-PROT (5)   
Protein domain (27)   
   InterPro (27)   
All databases (94)   

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