Chemistry:Saccharopine
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![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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| 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). | |
 verify (what is   ?)
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| Infobox references | |
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
The reactions involved, catalysed by saccharopine dehydrogenases, are:
- lysine + alpha-ketoglutarate ⇌ saccharopine ⇌ glutamate + 2-aminoadipate 6-semialdehyde
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 yeasts (Saccharomyces, hence the name) by Darling and Larsen.[2]
See also
- Opines
References
- ↑ "N-(5-AMINO-5-CARBOXYPENTYL)GLUTAMIC ACID - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 23 June 2005. Identification. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1087&loc=ec_rcs. 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).
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