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Information on EC 2.3.1.111 - mycocerosate synthase for references in articles please use BRENDA:EC2.3.1.111
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EC Tree
IUBMB Comments 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.
The enzyme appears in viruses and cellular organisms
Reaction Schemes
a long-chain acyl-[mycocerosic acid synthase]
+
3
+
6
+
6
=
a trimethylated-mycocerosoyl-[mycocerosate synthase]
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3
+
3
+
6
+
3
a long-chain acyl-[mycocerosic acid synthase]
+
4
+
8
+
8
=
a tetramethylated-mycocerosoyl-[mycocerosate synthase]
+
4
+
4
+
8
+
4
Synonyms
mycocerosic acid synthase,
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mycocerosic acid synthase
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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
(1)
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-
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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
(2)
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Acyl group transfer
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long-chain acyl-[mycocerosic acid synthase]:methylmalonyl-CoA C-acyltransferase (mycocerosate-forming)
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.
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eicosanoyl-CoA + 4 methylmalonyl-CoA + 4 NADPH
2,4,6,8-tetramethyloctacosanoyl-CoA + 4 CoA + 4 CO2 + 4 NADP+
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-
-
-
?
eicosanoyl-CoA + 4 methylmalonyl-CoA + 8 NADPH + 8 H+
tetramethyl-branched mycocerosoyl-CoA + 4 CoA + 4 CO2 + 8 NADP+ + 4 H2O
hexanoyl-CoA + methylmalonyl-CoA + NADPH
?
-
best substrate
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-
?
eicosanoyl-CoA + 4 methylmalonyl-CoA + 8 NADPH + 8 H+
tetramethyl-branched mycocerosoyl-CoA + 4 CoA + 4 CO2 + 8 NADP+ + 4 H2O
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-
-
-
?
eicosanoyl-CoA + 4 methylmalonyl-CoA + 8 NADPH + 8 H+
tetramethyl-branched mycocerosoyl-CoA + 4 CoA + 4 CO2 + 8 NADP+ + 4 H2O
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multifunctional enzyme, specific for methylmalonyl-CoA, cannot be replaced by malonyl-CoA, n-acyl-CoAs of C-6 to C-20 are substrates
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-
?
eicosanoyl-CoA + 4 methylmalonyl-CoA + 8 NADPH + 8 H+
tetramethyl-branched mycocerosoyl-CoA + 4 CoA + 4 CO2 + 8 NADP+ + 4 H2O
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fatty acid biosynthesis
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?
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eicosanoyl-CoA + 4 methylmalonyl-CoA + 8 NADPH + 8 H+
tetramethyl-branched mycocerosoyl-CoA + 4 CoA + 4 CO2 + 8 NADP+ + 4 H2O
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fatty acid biosynthesis
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?
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bovine serum albumin
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-
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CoA
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1 mM, weak inhibition
NADPH
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above 0.5 mM, weak inhibition
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brenda
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brenda
var. bovis Bacillus Calmette-Guerin
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238000
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2 * 238000, SDS-PAGE
238000
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2 * 238000, amino acid composition
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dimer
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2 * 238000, SDS-PAGE
dimer
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2 * 238000, amino acid composition
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Glycerol
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stable in 10% glycerol
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-20�C, glycerol-buffer, stable for at least 1 month
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Rainwater, D.L.; Kolattokudy, P.E.
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
J. Biol. Chem.
260
616-623
1985
Mycobacterium tuberculosis, Mycolicibacterium smegmatis
brenda
Mathur, M.; Kolattokudy, P.E.
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
J. Biol. Chem.
267
19388-19395
1992
Mycobacterium tuberculosis
brenda
Fitzmaurice, A.M.; Kolattukudy, P.E.
An acyl-CoA synthase (acoas) gene adjacent to the mycocerosic acid synthase (mas) locus is necessary for mycocerosyl lipid synthesis in Mycobacterium tuberculosis var. bovis BCG
J. Biol. Chem.
273
8033-8039
1998
Mycobacterium tuberculosis
brenda
Fernandes, N.D.; Kolattukudy, P.E.
A newly identified methyl-branched chain fatty acid synthesizing enzyme from Mycobacterium tuberculosis var. bovis BCG
J. Biol. Chem.
273
2823-2828
1998
Mycobacterium tuberculosis
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Li, M.S.; Monahan, I.M.; Waddell, S.J.; Mangan, J.A.; Martin, S.L.; Everett, M.J.; Butcher, P.D.
cDNA-RNA subtractive hybridization reveals increased expression of mycocerosic acid synthase in intracellular Mycobacterium bovis BCG
Microbiology
147
2293-2305
2001
Mycobacterium tuberculosis
brenda
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