Saccharopine

Summary

Saccharopine is an intermediate in the metabolism of amino acid lysine. It is a precursor of lysine in the alpha-aminoadipate pathway which occurs in fungi and euglenids. In mammals and higher plants saccharopine is an intermediate in the degradation of lysine, formed by condensation of lysine and alpha-ketoglutarate.

Saccharopine
Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino})
Names
IUPAC name
2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid[1]
Identifiers
  • 997-68-2 ☒N
3D model (JSmol)
  • Interactive image
3DMet
  • B01246
ChEBI
  • CHEBI:16927 checkY
ChemSpider
  • 141086 checkY
DrugBank
  • DB04207 checkY
KEGG
  • C00449 ☒N
MeSH saccharopine
  • 160556
UNII
  • WBQ73O8W32 ☒N
  • InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19) ☒N
    Key: ZDGJAHTZVHVLOT-UHFFFAOYSA-N ☒N
  • NC(CCCCNC(CCC(=O)O)C(=O)O)C(=O)O
Properties
C11H20N2O6
Molar mass 276.289 g·mol−1
Related compounds
Related alkanoic acids
Related compounds
Palmitoylethanolamide
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

Reaction edit

The reactions involved, catalysed by saccharopine dehydrogenases, are:

lysine + alpha-ketoglutarate ⇌ saccharopine ⇌ glutamate + 2-aminoadipate 6-semialdehyde

Pathology edit

Saccharopinuria (high amounts of saccharopine in the urine) and saccharopinemia (an excess of saccharopine in the blood) are conditions present in some inherited disorders of lysine degradation.

History edit

Saccharopine was first isolated in 1961 from yeasts (Saccharomyces, hence the name) by Darling and Larsen.[2]

See also edit

References edit

  1. ^ "N-(5-AMINO-5-CARBOXYPENTYL)GLUTAMIC ACID - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 23 June 2005. Identification. Retrieved 11 July 2012.
  2. ^ Darling, S., and Larsen, P. O., Saccharopine, a new amino acid in Baker's and Brewer's yeast: I. Isolation and properties. Acta Chem. Scand., 15, 743 (1961).