Saccharopine

Quality 0.50 · 1 view · Updated 2 months ago

title: "Saccharopine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["tricarboxylic-acids"] topic_path: "general/tricarboxylic-acids" source: "https://en.wikipedia.org/wiki/Saccharopine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464385925 | ImageFile = Saccharopine.svg | ImageFile_Ref = | ImageName = Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino}) | IUPACName = 2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid | Section1 = {{Chembox Identifiers | CASNo = 997-68-2 | CASNo_Ref = | UNII_Ref = | UNII = WBQ73O8W32 | PubChem = 160556 | ChemSpiderID = 141086 | ChemSpiderID_Ref = | DrugBank = DB04207 | DrugBank_Ref = | KEGG = C00449 | KEGG_Ref = | MeSHName = saccharopine | ChEBI = 16927 | ChEBI_Ref = | 3DMet = B01246 | SMILES = NC(CCCCNC(CCC(=O)O)C(=O)O)C(=O)O | StdInChI = 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) | StdInChI_Ref = | StdInChIKey = ZDGJAHTZVHVLOT-UHFFFAOYSA-N | StdInChIKey_Ref = | Section2 = {{Chembox Properties | C=11 | H=20 | N=2 | O=6 | Section3 = {{Chembox Related | OtherFunction_label = alkanoic acids | OtherFunction = | OtherCompounds = Palmitoylethanolamide

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.

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 baker's yeast (Saccharomyces cerevisiae, hence the name) by Darling and Larsen.

References

References

  1. (23 June 2005). "N-(5-AMINO-5-CARBOXYPENTYL)GLUTAMIC ACID - Compound Summary". National Center for Biotechnology Information.
  2. 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).

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

tricarboxylic-acids