Saccharopine

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Saccharopine
Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino})
Identifiers
CAS number 997-68-2 YesY
PubChem 160556
ChemSpider 141086 YesY
DrugBank DB04207
KEGG C00449 YesY
MeSH saccharopine
ChEBI CHEBI:16927 YesY
3DMet B01246
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C11H20N2O6
Molar mass 276.29 g mol−1
Related compounds
Related alkanoic acids
Related compounds Palmitoylethanolamide
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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 a few lower fungi, the higher 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]

  1. ^ "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. 
  2. ^ 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).