Semialdehyde

In organic chemistry, a semialdehyde is a compound containing an aldehyde and a carboxylic acid functional groups. Semialdehydes are common in biochemistry.[1] The simplest semialdehydes have the formula HO2C(CH2)nCHO. As illustrated by the behavior of the smallest member, glyoxylic acid, semialdehydes often exist as hydrates (geminal diols) HO2C(CH2)nCH(OH)2.

Some of semialdehydes and their parent dicarboxylic acids are listed below.

Selected Semialdehydes and their parent diacid
SemialdehydeDicarboxylic acid
malonic semialdehyde malonic acid
tartronic semialdehyde tartronic acid
succinic semialdehyde succinic acid
methylmalonic semialdehyde methylmalonic acid
aspartic-4-semialdehyde aspartic acid
glutamic-1-semialdehyde glutamic acid
glutamic-5-semialdehyde glutamic acid
4-hydroxymuconic-semialdehyde 4-Hydroxymuconic acid
2-amino-3-carboxymuconic semialdehyde 2-hydroxy-4-carboxymuconic acid
alpha-aminoadipic semialdehyde alpha-aminoadipic acid

Although structurally related to semialdehydes, dicarboxylic acids are rarely biochemical precursors to them.

References

  1. Requena, J. R.; Levine, R. L.; Stadtman, E. R. (2003). "Recent Advances in the Analysis of Oxidized Proteins". Amino Acids. 25 (3–4): 221–226. doi:10.1007/s00726-003-0012-1. PMID 14661085. S2CID 28837698.
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