Saccharopine

Saccharopine

Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino})
Names
IUPAC name 2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid
Identifiers
CAS Number	997-68-2  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16927  Y
ChemSpider	141086  Y
DrugBank	DB04207  Y
KEGG	C00449  Y
MeSH	saccharopine
PubChem CID	160556
UNII	WBQ73O8W32  Y
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) Y Key: ZDGJAHTZVHVLOT-UHFFFAOYSA-N Y
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). 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 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]}

L-lysine

+

 

α-Ketoglutaric acid

 

 

 

 

 

 

Saccharopine

 

 

 

 

 

 

 

L-glutamic acid

+

 

L-allysine

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

• Opines

References

1. 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.
2. 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.
3. 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.
4. Higashino, K. (1998). "Saccharopinuria (a variant form of familial hyperlysinemia)". Ryoikibetsu Shokogun Shirizu (18 Pt 1): 191–4. PMID   9590025.
5. 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).