Saccharopine (original) (raw)
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Saccharopine
[![Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino})](http://upload.wikimedia.org/wikipedia/commons/thumb/2/25/Saccharopine.PNG/250px-Saccharopine.PNG) ](/wiki/File:Saccharopine.PNG "Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino})")Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino}) |
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| Names | |
| IUPAC name 2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid[1] | |
| Identifiers | |
| CAS Number | 997-68-2  N |
| 3D model (JSmol) | Interactive image |
| ChEBI | CHEBI:16927  Y |
| ChemSpider | 141086 Y |
| DrugBank | DB04207 Y |
| KEGG | C00449 N |
| MeSH | saccharopine |
| PubChem CID | 160556 |
| UNII | WBQ73O8W32 N |
| CompTox Dashboard (EPA) | DTXSID80862507  |
| InChI 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) NKey: ZDGJAHTZVHVLOT-UHFFFAOYSA-N N |
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| SMILES NC(CCCCNC(CCC(=O)O)C(=O)O)C(=O)O | |
| Properties | |
| Chemical formula | C11H20N2O6 |
| Molar mass | 276.289 g·mol−1 |
| Related compounds | |
| Related alkanoic acids | 4-(γ-Glutamylamino)butanoic acidHypusine |
| Related compounds | Palmitoylethanolamide |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references |
Chemical compound
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.
The reactions involved, catalysed by saccharopine dehydrogenases, are:
lysine + alpha-ketoglutarate ⇌ saccharopine ⇌ glutamate + 2-aminoadipate 6-semialdehyde
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.
Saccharopine was first isolated in 1961 from yeasts (Saccharomyces, hence the name) by Darling and Larsen.[2]
- ^ "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).