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
YROCH64_296
AQSDKK66_17805
BOBGN304_08335
BOMBGT348_07885
MTURv3825c(pks2)
MTVRVBD_3825c
MTCMT3933(mas-3)
MRAMRA_3865(pks2)
MTFTBFG_13859
MTBTBMG_03872
MTKTBSG_03895
MTZTBXG_003842
MTECCDC5079_3555
MTURCFBS_4055
MTLCCDC5180_3504
MTOMTCTRI2_3904(pks2)
MTDUDA_3825c(pks2)
MTNERDMAN_4192(pks2)
MTJJ112_20565
MTUBMT7199_3894
MTUEJ114_20440
MTXM943_19640
MTUHI917_26895
MTULTBHG_03763
MTUTHKBT1_4038(pks2)
MTUUHKBT2_4048(pks2)
MTQHKBS1_4051(pks2)
MBOBQ2027_MB3855C(pks2)
MBBBCG_3888c(pks2)
MBTJTY_3890(pks2)
MBMBCGMEX_3889c(pks2)
MBKK60_039690
MBXBCGT_3690
MAFMAF_38400(pks2)
MMICRN08_4223
MCEMCAN_38441(pks2)
MCQBN44_120235(pks)
MCVBN43_90342(pks)
MCXBN42_90353(pks)
MCZBN45_110187(pks)
MPAMAP_3764c(pks2)
MBAIMB901379_03143(pks2_3)
MGAUMGALJ_24090(pks2)
NFANFA_30250
NFRERS450000_01048(pks2_1)
NCYNOCYR_3144
NBRO3I_032485
NNONONO_c02170
AEYCDG81_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

DBGET integrated database retrieval system