Saccharopine
![Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino})](/wiki/File:Saccharopine.PNG)
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| Names | |
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| IUPAC name
2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid[1]
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| Identifiers | |
3D model (JSmol)
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| DrugBank | |
| KEGG | |
| MeSH | saccharopine |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C11H20N2O6 | |
| Molar mass | 276.289 g·mol−1 |
| Related compounds | |
Related alkanoic acids
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Related compounds
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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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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.
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]- ^ "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.
- ^ 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).