Saccharopine
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| IUPAC name
2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid
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3D model (JSmol)
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| 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).
Infobox references
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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 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:[1][2][3]
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
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Higashino, K. (1998). "Saccharopinuria (a variant form of familial hyperlysinemia)". Ryoikibetsu Shokogun Shirizu (18 Pt 1): 191–4. PMID 9590025.
- ^ 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).