Saccharopine

Names
IUPAC name 2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid[1]
Identifiers
CAS Number	997-68-2 N
3D model (JSmol)	Interactive image
3DMet	B01246
ChEBI	CHEBI:16927 Y
ChemSpider	141086 Y
DrugBank	DB04207 Y
KEGG	C00449 N
MeSH	saccharopine
PubChem CID	160556
UNII	WBQ73O8W32 N
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) N Key: ZDGJAHTZVHVLOT-UHFFFAOYSA-N N
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 acid Hypusine
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

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]

• Opines

References[edit]