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Saccharopine

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Saccharopine
Names
Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino})
IUPAC name 2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid^[1]
Identifiers
CAS Number	997-68-2^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16927^Y
ChemSpider	141086^Y
DrugBank	DB04207^Y
KEGG	C00449^N
MeSH	saccharopine
PubChem CID	160556
UNII	WBQ73O8W32^N
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)^N Key: ZDGJAHTZVHVLOT-UHFFFAOYSA-N^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 theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Saccharopine is an intermediate in themetabolism of amino acidlysine. It is a precursor of lysine in thealpha-aminoadipate pathway which occurs infungi andeuglenids. In mammals andseed plants saccharopine is an intermediate in the degradation of lysine, formed by condensation of lysine andalpha-ketoglutarate.

Reaction

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The reactions involved, catalysed bysaccharopine dehydrogenases, are:

lysine + alpha-ketoglutarate ⇌ saccharopine ⇌ glutamate +2-aminoadipate 6-semialdehyde

Pathology

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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

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Saccharopine was first isolated in 1961 frombaker's yeast (Saccharomyces cerevisiae, hence the name) by Darling and Larsen.^[2]

References

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^"N-(5-AMINO-5-CARBOXYPENTYL)GLUTAMIC ACID - Compound Summary".PubChem Compound. USA: National Center for Biotechnology Information. 23 June 2005. Identification. Retrieved11 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 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-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 α-Ketobutyric acid +Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA