Saccharopine

Chemical compound From Wikipedia, the free encyclopedia

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 seed plants saccharopine is an intermediate in the degradation of lysine, formed by condensation of lysine and alpha-ketoglutarate.

Quick facts Names, Identifiers ...
Saccharopine
Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino})
Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino})
Names
IUPAC name
2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
KEGG
MeSH saccharopine
UNII
  • 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) checkY
    Key: ZDGJAHTZVHVLOT-UHFFFAOYSA-N checkY
  • 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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Biochemical reactions

The reactions involved, catalysed by saccharopine dehydrogenases, are:[1][2][3]

2D representation of the chemical structure of Q20816880.
L-lysine
+
 
2D representation of the chemical structure of α-Ketoglutaric acid .
α-Ketoglutaric acid
 
 
 
Reversible left-right reaction arrow
 
 
 
Saccharopine
 
 
 
 
Reversible left-right reaction arrow
 
 
 
2D representation of the chemical structure of Q26995161.
L-glutamic acid
+
 
2D representation of the chemical structure of Q28529674.
L-allysine

Pathology

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.[4]

History

Saccharopine was first isolated in 1961 from baker's yeast (Saccharomyces cerevisiae, hence the name) by Darling and Larsen.[5]

See also

References

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