KEGG ENZYME: 2.3.1.111

ENZYME: 2.3.1.111

Entry

EC 2.3.1.111                Enzyme

Name

mycocerosate synthase;
mas (gene name);
mycocerosic acid synthase;
acyl-CoA:methylmalonyl-CoA C-acyltransferase (decarboxylating, oxoacyl- and enoyl-reducing);
long-chain acyl-CoA:methylmalonyl-CoA C-acyltransferase (mycocerosate-forming)

Class

Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups

Sysname

long-chain acyl-[mycocerosic acid synthase]:methylmalonyl-CoA C-acyltransferase (mycocerosate-forming)

Reaction(IUBMB)

(1) a long-chain acyl-[mycocerosic acid synthase] + 3 methylmalonyl-CoA + 6 NADPH + 6 H+ = a trimethylated-mycocerosoyl-[mycocerosate synthase] + 3 CoA + 3 CO2 + 6 NADP+ + 3 H2O;
(2) a long-chain acyl-[mycocerosic acid synthase] + 4 methylmalonyl-CoA + 8 NADPH + 8 H+ = a tetramethylated-mycocerosoyl-[mycocerosate synthase] + 4 CoA + 4 CO2 + 8 NADP+ + 4 H2O

Reaction(KEGG)

(other) R05189 R11450

Substrate

long-chain acyl-[mycocerosic acid synthase];
methylmalonyl-CoA [CPD:C02557];
NADPH [CPD:C00005];
H+ [CPD:C00080]

Product

trimethylated-mycocerosoyl-[mycocerosate synthase];
CoA [CPD:C00010];
CO2 [CPD:C00011];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
tetramethylated-mycocerosoyl-[mycocerosate synthase]

Comment

The enzyme, characterized from mycobacteria, is loaded with a long-chain acyl moiety by EC 6.2.1.49, long-chain fatty acid adenylyltransferase FadD28, and elongates it by incorporation of three or four methylmalonyl (but not malonyl) residues, to form tri- or tetramethyl-branched fatty-acids, respectively, such as 2,4,6,8-tetramethyloctacosanoate (C32-mycocerosate). Since the enzyme lacks a thioesterase domain, the product remains bound and requires additional enzyme(s) for removal. Even though the enzyme can accept C6 to C20 substrates in vitro, it prefers to act on C14-C20 substrates in vivo.

History

EC 2.3.1.111 created 1989, modified 2016, modified 2017

Orthology

K11628

mycocerosic acid synthase

Genes

GOH:

B932_3088

GTI:	FXF46_12120

MTU:	Rv2940c(mas)

MTV:	RVBD_2940c

MTC:	MT3010(mas-2)

MRA:	MRA_2966(mas)

MTF:	TBFG_12954

MTB:	TBMG_01032

MTK:	TBSG_01040

MTZ:	TBXG_001020

MTG:	MRGA327_18070

MTE:	CCDC5079_2700

MTUR:

CFBS_3098(mas)

MTL:	CCDC5180_2664

MTO:	MTCTRI2_2997(mas)

MTD:	UDA_2940c(mas)

MTN:	ERDMAN_3222(mas)

MTJ:	J112_15735

MTUB:

MT7199_2974

MTUE:

J114_15700

MTX:	M943_15160

MTUL:

TBHG_02870

MTUT:

HKBT1_3086(mas)

MTUU:

HKBT2_3091(mas)

MTQ:	HKBS1_3093(mas)

MBO:	BQ2027_MB2965C(mas)

MBB:	BCG_2962c(mas)

MBT:	JTY_2957(mas)

MBM:	BCGMEX_2957c(mas)

MBK:	K60_030450

MBX:

BCGT_2778

MAF:	MAF_29450(mas)

MMIC:

RN08_3240

MCE:	MCAN_29621(mas)

MCQ:	BN44_60417(mas)

MCV:	BN43_40648(mas)

MCX:	BN42_40938(mas)

MCZ:	BN45_51352(mas)

MORY:

MO_003072(mas)

MLE:	ML0139(mas)

MLB:	MLBr00139(mas)

MUL:	MUL_2010(mas)

MMI:	MMAR_1767(mas)

MMAE:

MMARE11_16870(mas)

MLI:	MULP_01923(mas)

MPSE:

MPSD_40670(mas)

MSHO:

MSHO_54730(mas)

MKN:	MKAN_23980

MHAD:

B586_03330

MSHG:

MSG_01621(mas)

MFJ:	MFLOJ_16850(mas)

MSIM:

MSIM_07840(mas)

MLW:	MJO58_08780

MPAG:

C0J29_10270

MGOR:

H0P51_01940

MBAI:

MB901379_01582(mas)

MGAU:

MGALJ_49480(mas)

MLJ:	MLAC_28780(mas)

MSHJ:

MSHI_07270(mas)

MMAM:

K3U93_07795

MSPG:

F6B93_07120

MOT:	LTS72_16020

MLM:	MLPF_0168(mas)

MHOL:

K3U96_18775

SRT:

Srot_0318

» show all

Reference

1 [PMID:3880746]

Authors

Rainwater DL, Kolattukudy PE.

Title

Fatty acid biosynthesis in Mycobacterium tuberculosis var. bovis Bacillus Calmette-Guerin. Purification and characterization of a novel fatty acid synthase, mycocerosic acid synthase, which elongates n-fatty acyl-CoA with methylmalonyl-CoA.

Journal

J Biol Chem 260:616-23 (1985)

Sequence

[mbo:BQ2027_MB2965C]

Reference

2 [PMID:1527058]

Authors

Mathur M, Kolattukudy PE

Title

Molecular cloning and sequencing of the gene for mycocerosic acid synthase, a novel fatty acid elongating multifunctional enzyme, from Mycobacterium tuberculosis var. bovis Bacillus Calmette-Guerin.

Journal

J Biol Chem 267:19388-95 (1992)

Sequence

[mbo:BQ2027_MB2965C]

Reference

3 [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