Malonyl-CoA

Malonyl-CoA
Identifiers
CAS Number	524-14-1 ;
ChemSpider	10213 ;
ECHA InfoCard	100.007.596
MeSH	Malonyl+CoA
PubChem CID	869;
CompTox Dashboard (EPA)	DTXSID40904351 ;
	InChI 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 Key: LTYOQGRJFJAKNA-VFLPNFFSSA-N ;
Properties
Chemical formula	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).
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	Infobox references

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.

Fatty acid biosynthesis

In the former, it 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 malonyl coenzyme A:acyl carrier protein transacylase (MCAT). MCAT serves to transfer malonate from malonyl-CoA to the terminal thiol of holo-acyl carrier protein (ACP).

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 beta-oxidation of fatty acids. Malonyl-CoA inhibits fatty acids from associating with carnitine by regulating the enzyme carnitine acyltransferase, thereby preventing them from entering the mitochondria, where fatty acid oxidation and degradation occur.

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References

Nelson D, Cox M (2008) Lehninger principles of biochemistry. 5th Ed: p. 806

External links

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[1] Nelson D, Cox M (2008) Lehninger principles of biochemistry. 5th Ed: p. 806