Malonyl-CoA

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Malonyl-CoA
Names
Preferred IUPAC name
(9R)-1-[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]-3,5,9-trihydroxy-3,5,10,14,19-pentaoxo-8,8-dimethyl-2,4,6-trioxa-18-thia-11,15-diaza-3λ5,5λ5-diphosphahenicosan-21-oic acid
Identifiers
ChemSpider
ECHA InfoCard
 100.007.596 Edit this at Wikidata
MeSH Malonyl+CoA
UNII
  • InChI=1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19+,23-/m1/s1 checkY
    Key: LTYOQGRJFJAKNA-DVVLENMVSA-N checkY
Properties
C24H38N7O19P3S
Molar mass 853.582
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Malonyl-CoA is a coenzyme A derivative of malonic acid.

Functions

It plays a key role in chain elongation in

fatty acid biosynthesis and polyketide
biosynthesis.

Cytosolic fatty acid biosynthesis

Malonyl-CoA provides 2-carbon units to fatty acids and commits them to fatty acid chain synthesis.

Malonyl-CoA is formed by carboxylating acetyl-CoA using the enzyme acetyl-CoA carboxylase. One molecule of acetyl-CoA joins with a molecule of bicarbonate,[1] requiring energy rendered from ATP.

Malonyl-CoA is utilised in fatty acid biosynthesis by the enzyme

malonate from malonyl-CoA to the terminal thiol of holo-acyl carrier protein
(ACP).

Mitochondrial fatty acid synthesis

Malonyl-CoA is formed in the first step of mitochondrial fatty acid synthesis (mtFASII) from malonic acid by malonyl-CoA synthetase (ACSF3).[2][3]

Polyketide biosynthesis

MCAT is also involved in bacterial polyketide biosynthesis. The enzyme MCAT together with an acyl carrier protein (ACP), and a polyketide synthase (PKS) and chain-length factor heterodimer, constitutes the minimal PKS of type II polyketides.

Regulation

Malonyl-CoA is a highly regulated molecule in fatty acid synthesis; as such, it inhibits the rate-limiting step in

fatty acid oxidation
and degradation occur.

Related diseases

Malonyl-CoA plays a special role in the mitochondrial clearance of toxic malonic acid in the metabolic disorder combined malonic and methylmalonic aciduria (CMAMMA).[4] In CMAMMA due to ACSF3, malonyl-CoA synthetase is decreased, which can generate malonyl-CoA from malonic acid, which can then be converted to acetyl-CoA by malonyl-CoA decarboxylase.[2][4] In contrast, in CMAMMA due to malonyl-CoA decarboxylase deficiency, malonyl-CoA decarboxylase is decreased, which converts malonyl-CoA to acetyl-CoA.[4]


See also

References

  1. ^ Nelson D, Cox M (2008). Lehninger principles of biochemistry (5th ed.). p. 806.
  2. ^
    PMID 21846720
    .
  3. PMID 28479296
    .
  4. ^
    PMID 30201289
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Malonyl-CoA&oldid=1212337465"