Tartronic acid semialdehyde

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Tartronic acid semialdehyde
Names
Other names
Tartronaldehydic acid
2-hydroxy-3-oxopropanoic acid
formyl(hydroxy)acetic acid
Hydroxymalonaldehydic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h1-2,5H,(H,6,7)
    Key: QWBAFPFNGRFSFB-UHFFFAOYSA-N
  • C(=O)C(C(=O)O)O
Properties
C3H4O4
Molar mass 104.061 g·mol−1
Appearance white solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tartronic acid semialdehyde is the organic compound with the formula OCHCH(OH)CO2H. The molecule has three functional groups, aldehyde, alcohol, and carboxylic acid. A white solid, it occurs naturally. A near neutral pH, it exists as the hydrated carboxylate (HO)2CHCH(OH)CO2−, which is referred to as tartronate semialdehyde. Tartronate semialdehyde is produced and consumed on a prodigious scale as an intermediate in photorespiration, an undesirable side reaction that competes with photosynthesis. It is produced biologically by the condensation of two equivalents of glyoxalate:[1]

2 OC(H)CO2H → OC(H)CH(OH)CO2H + CO2

This condensation is catalyzed by tartronate-semialdehyde synthase.

References

  1. ^ Leegood RC (May 2007). "A Welcome Diversion from Photorespiration". Nature Biotechnology. 25 (5): 539–40. doi:10.1038/nbt0507-539. PMID 17483837. S2CID 5015366.
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