Saccharopine

Saccharopine
Names
	IUPAC name 2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid
Identifiers
CAS Number	997-68-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16927 ;
ChemSpider	141086 ;
DrugBank	DB04207 ;
KEGG	C00449 ;
MeSH	saccharopine
PubChem CID	160556;
UNII	WBQ73O8W32 ;
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) Key: ZDGJAHTZVHVLOT-UHFFFAOYSA-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). verify (what is ?) 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

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.^[2]

References

^ "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).

[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).

[1]

[2]

Reaction

Pathology

History

See also

References