Methylmalonic acid semialdehyde

Methylmalonic acid semialdehyde

Names
Preferred IUPAC name 2-Methyl-3-oxopropanoic acid
Other names Methylmalonate semialdehyde, 2-methyl-3-oxopropanoic acid
Identifiers
CAS Number	6236-08-4  Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:16256  Y
ChemSpider	290  Y
KEGG	C00349  Y
PubChem CID	296
UNII	036CTC7X1V  Y
CompTox Dashboard (EPA)	DTXSID60274265
InChI InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7) Y Key: VOKUMXABRRXHAR-UHFFFAOYSA-N Y InChI=1/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7) Key: VOKUMXABRRXHAR-UHFFFAOYAB
SMILES CC(C=O)C(=O)O O=CC(C(=O)O)C
Properties
Chemical formula	C4H6O3
Molar mass	102.09 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methylmalonic acid semialdehyde is an intermediate in the metabolism of thymine and valine. ^[1] It is a substrate of the enzyme methylmalonate-semialdehyde dehydrogenase (acylating), which converts it to propionyl-CoA. ^{[2] [3] [4]}

Methylmalonic acid semialdehyde

+ CoA + NAD⁺

 

 

 

CO₂ + H⁺

 

CO₂ + H⁺

 

Propionyl-CoA

+ NADH

 

References

1. Voet, Donald (2011). Biochemistry. Judith G. Voet (4th ed.). Hoboken, NJ: John Wiley & Sons. ISBN   978-0-470-57095-1. OCLC   690489261.
2. Enzyme 1.2.1.27 at KEGG Pathway Database.
3. Sokatch JR, Sanders LE, Marshall VP (1968). "Oxidation of methylmalonate semialdehyde to propionyl coenzyme A in Pseudomonas aeruginosa grown on valine". J. Biol. Chem. 243 (10): 2500–6. doi: 10.1016/S0021-9258(18)93403-4 . PMID   4297649.
4. Stines-Chaumeil C, Talfournier F, Branlant G (2006). "Mechanistic characterization of the MSDH (methylmalonate semialdehyde dehydrogenase) from Bacillus subtilis". Biochem. J. 395 (1): 107–15. doi:10.1042/BJ20051525. PMC   1409689 . PMID   16332250.