KEGG ENZYME: 2.3.1.287

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

LinkDB

DBGET integrated database retrieval system