Saccharopine

Saccharopine
Names

IUPAC name 2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid^[1]
Identifiers
CAS Number	997-68-2^N
3D model (Jmol)	Interactive image Interactive image
3DMet	B01246
ChEBI	CHEBI:16927^Y
ChemSpider	141086^Y
DrugBank	DB04207^Y
KEGG	C00449^N
MeSH	saccharopine
PubChem	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]):[oH])c(:[o]):[oH])c(:[o]):[oH] NC(CCCCNC(CCC(O)=O)C(O)=O)C(O)=O
Properties
Chemical formula	C₁₁H₂₀N₂O₆
Molar mass	276.29 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 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.^[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).

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid β-hydroxy β-methylbutyric acid β-hydroxy β-methylbutyryl-CoA Isovaleryl-CoA 3-Methylcrotonyl-CoA 3-Methylglutaconyl-CoA HMG-CoA

tryptophan→alanine→	N'-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→citrate

glycine→serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid

isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA

methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

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Saccharopine

Reaction

Pathology

History

See also

References