KEGG   ENZYME: 2.3.1.111Help
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)
Class
Transferases;
Acyltransferases;
Transferring groups other than aminoacyl groups
BRITE hierarchy
Sysname
long-chain acyl-CoA:methylmalonyl-CoA C-acyltransferase (mycocerosate-forming)
Reaction(IUBMB)
(1) a long-chain acyl-CoA + 3 methylmalonyl-CoA + 6 NADPH + 6 H+ + mycocerosate synthase = a trimethylated-mycocerosoyl-[mycocerosate synthase] + 4 CoA + 3 CO2 + 6 NADP+ + 3 H2O;
(2) a long-chain acyl-CoA + 4 methylmalonyl-CoA + 8 NADPH + 8 H+ + mycocerosate synthase = a tetramethylated-mycocerosoyl-[mycocerosate synthase] + 5 CoA + 4 CO2 + 8 NADP+ + 4 H2O
Reaction(KEGG)
(other) R05189
Show
Substrate
long-chain acyl-CoA [CPD:C02843];
methylmalonyl-CoA [CPD:C02557];
NADPH [CPD:C00005];
H+ [CPD:C00080];
mycocerosate synthase
Product
trimethylated-mycocerosoyl-[mycocerosate synthase];
CoA [CPD:C00010];
CO2 [CPD:C00011];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
tetramethylated-mycocerosoyl-[mycocerosate synthase]
Comment
This mycobacterial enzyme loads long-chain fatty acyl groups from their CoA esters and extends them 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 products remain bound to the enzyme and require 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
Orthology
K11628  
mycocerosic acid synthase
Genes
MTU: 
Rv2940c(mas)
MTV: 
MTC: 
MT3010(mas-2)
MRA: 
MTF: 
MTB: 
MTK: 
MTZ: 
MTG: 
MTE: 
MTUR: 
MTL: 
MTO: 
MTD: 
MTN: 
MTJ: 
MTUB: 
MTUE: 
MTX: 
MTUL: 
MTUT: 
MTUU: 
MTQ: 
MBO: 
Mb2965c(mas)
MBB: 
MBT: 
MBM: 
MBK: 
MBX: 
MBZ: 
MAF: 
MCE: 
MCQ: 
MCV: 
MCX: 
MCZ: 
MMIC: 
MLE: 
ML0139(mas)
MLB: 
MUL: 
MMI: 
MLI: 
MKN: 
MKS: 
MKI: 
MHAD: 
SLE: 
sle_14460(sle_14460)
KPHY: 
 » show all
Taxonomy
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 (1985) 616-23.
  Sequence
[mbo: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 (1992) 19388-95.
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 (2005) 631-43.
Reference
4  [PMID:24831705]
  Authors
Menendez-Bravo S, Comba S, Sabatini M, Arabolaza A, Gramajo H
  Title
Expanding the chemical diversity of natural esters by engineering a polyketide-derived pathway into Escherichia coli.
  Journal
Metab. Eng. 24 (2014) 97-106.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
95229-19-9

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