Saccharopine

Saccharopine
IUPAC name 2-[(5-amino-5-carboxy-pentyl) amino] pentanedioic acid
Identifiers
CAS number	997-68-2
PubChem	160556
ChemSpider	141086 Y
DrugBank	DB04207
MeSH	Saccharopine
ChEBI	CHEBI:16927 Y
Jmol-3D images	Image 1
SMILES O=C(O)[C@@H](N)CCCCN[C@H](C(=O)O)CCC(=O)O
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)/t7-,8-/m0/s1 Y Key: ZDGJAHTZVHVLOT-YUMQZZPRSA-N Y InChI=1/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)/t7-,8-/m0/s1 Key: ZDGJAHTZVHVLOT-YUMQZZPRBV
Properties
Molecular formula	C11H20N2O6
Molar mass	276.286
Boiling point	257-259°C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

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.

See also

• Opines