Saccharopine

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Saccharopine
IUPAC name	2-[(5-amino-5-carboxy-pentyl) amino] pentanedioic acid
Identifiers
CAS number	[997-68-2]
PubChem	1087
MeSH	Saccharopine
SMILES	C(CCNC(CCC(=O)O)C(=O)O)CC(C(=O)O)N
Properties
Molecular formula	C11H20N2O6
Molar mass	276.286
Boiling point	257-259°C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.

Contents 1 Reaction 2 Pathology 3 History 4 See also 5 References

[edit] Reaction

The reactions involved, catalysed by saccharopine dehydrogenases, are:

lysine + alpha-ketoglutarate <--> saccharopine <--> glutamate + 2-aminoadipate 6-semialdehyde

[edit] 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.

[edit] History

Saccharopine was first isolated in 1961 from yeasts (Saccharomyces, hence the name) by Darling and Larsen.^[1]

[edit] See also

• Opines

[edit] References

1. ^ 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).

v • d • e Amino acid metabolism metabolic intermediates K→acetyl-CoA lysine→ Saccharopine - Allysine - Alpha-aminoadipate - Alpha-ketoadipic acid - Glutaryl-CoA - Glutaconyl-CoA - Crotonyl-CoA - Beta-hydroxybutyryl-CoA leucine→ Alpha-ketoisocaproic acid - 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→glutamate histidine→ Urocanic acid - Imidazol-4-one-5-propionic acid - Formiminoglutamic acid - Glutamate-1-semialdehyde proline→ 1-Pyrroline-5-carboxylic acid arginine→ Ornithine - Putrescine - Agmatine G→propionyl-CoA methionine→ S-Adenosyl methionine - S-Adenosyl-L-homocysteine - Homocysteine - Cystathionine - alpha-Ketobutyric acid isoleucine→ 2,3-Dihydroxy-3-methylpentanoic acid - 2-Methylbutyryl-CoA - Tiglyl-CoA - 2-methylacetoacetyl-CoA valine→ Alpha-ketoisovalerate - Isobutyryl-CoA - Methacrylyl-CoA - 3-Hydroxyisobutyryl-CoA - 3-Hydroxyisobutyrate - 2-methyl-3-oxopropanoate threonine→ Alpha-ketobutyric acid propionyl-CoA→ Methylmalonyl-CoA G→fumarate phenylalanine→tyrosine→ 4-Hydroxyphenylpyruvic acid - Homogentisic acid - 4-Maleylacetoacetate Other cysteine+glutamate→glutathione gamma-Glutamylcysteine glycine→creatine Glycocyamine - Phosphocreatine - Creatinine Other Glycerate 3-phosphate (serine) - Cysteine sulfinic acid see also enzymes, disorders