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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7) checkY
    Key: VOKUMXABRRXHAR-UHFFFAOYSA-N checkY
  • 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]

2D representation of the chemical structure of Methylmalonic acid semialdehyde.
Methylmalonic acid semialdehyde
+ CoA + NAD+
 
 
 
CO2 + H+
Reversible left-right reaction arrow with minor forward product(s) to top right and minor reverse substrate(s) from bottom right
 
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.
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