Saccharopine

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).

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.

Biochemical reactions

The reactions involved, catalysed by saccharopine dehydrogenases, are:

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.

History

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

See also

References

  1. ↑ Fujioka M, Nakatani Y (1972). "Saccharopine dehydrogenase. Interaction with substrate analogues". Eur. J. Biochem. 25 (2): 301–7. doi:10.1111/j.1432-1033.1972.tb01697.x. PMID 4339117.
  2. ↑ Saunders PP, Broquist HP (1966). "Saccharopine, an intermediate of the aminoadipic acid pathway of lysine biosynthesis. IV. Saccharopine dehydrogenase". J. Biol. Chem. 241 (14): 3435–40. doi:10.1016/S0021-9258(18)96483-5. PMID 4287986.
  3. ↑ Vashishtha AK, West AH, Cook PF (June 2009). "Chemical mechanism of saccharopine reductase from Saccharomyces cerevisiae". Biochemistry. 48 (25): 5899–907. doi:10.1021/bi900599s. PMID 19449898.
  4. ↑ Higashino, K. (1998). "Saccharopinuria (a variant form of familial hyperlysinemia)". Ryoikibetsu Shokogun Shirizu (18 Pt 1): 191–4. PMID 9590025.
  5. ↑ 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).