Saccharopine

Saccharopine

Chembox new
ImageFile=Saccharopine.gif
ImageSize=125px
IUPACName=2- [(5-amino-5-carboxy-pentyl) amino] pentanedioic acid
OtherNames=
Section1= Chembox Identifiers
CASNo=997-68-2
PubChem=1087
SMILES=C(CCNC(CCC(=O)O)C(=O)O)CC(C(=O)O)N
MeSHName=Saccharopine
Section2= Chembox Properties
Formula=C11H20N2O6
MolarMass=276.286
Appearance=
Density=
MeltingPt=
BoilingPt=257-259°C
Solubility=
Section3= Chembox Hazards
MainHazards=
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Autoignition=

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. [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).]

ee also

* Opines

References


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Look at other dictionaries:

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  • saccharopine — A derivative of α ketoglutarate and l lysine that is an intermediate in l lysine catabolism; elevated in cases of saccharopinuria. s. dehydrogenase two enzymes that are used in the pathway of l lysine catabolism; the first isoform catalyzes the… …   Medical dictionary

  • saccharopine dehydrogenase (NADP+ L-lysine-forming) — sac·cha·ro·pine de·hy·dro·gen·ase (NADP+, L ly·sine form·ing) (sakґə ro pēn″ de hiґdro jən ās liґsēn formґing) [EC 1.5.1.8] official nomenclature for lysine ketoglutarate reductase …   Medical dictionary

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