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Wikipedia

Saccharopine

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 higher plants saccharopine is an intermediate in the degradation of lysine, formed by condensation of lysine and alpha-ketoglutarate.

Saccharopine
Names
IUPAC name
2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid[1]
Identifiers
  • 997-68-2 N
3D model (JSmol)
  • Interactive image
3DMet
  • B01246
ChEBI
  • CHEBI:16927 Y
ChemSpider
  • 141086 Y
DrugBank
  • DB04207 Y
KEGG
  • C00449 N
MeSH saccharopine
  • 160556
UNII
  • WBQ73O8W32 N
  • 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
  • NC(CCCCNC(CCC(=O)O)C(=O)O)C(=O)O
Properties
C11H20N2O6
Molar mass 276.289 g·mol−1
Related compounds
Related alkanoic acids
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 ?)

Reaction edit

The reactions involved, catalysed by saccharopine dehydrogenases, are:

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

Pathology edit

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 edit

Saccharopine was first isolated in 1961 from yeasts (Saccharomyces, hence the name) by Darling and Larsen.[2]

See also edit

References edit

  1. ^ "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.
  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).

saccharopine, intermediate, metabolism, amino, acid, lysine, precursor, lysine, alpha, aminoadipate, pathway, which, occurs, fungi, euglenids, mammals, higher, plants, saccharopine, intermediate, degradation, lysine, formed, condensation, lysine, alpha, ketogl. 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 higher plants saccharopine is an intermediate in the degradation of lysine formed by condensation of lysine and alpha ketoglutarate Saccharopine NamesIUPAC name 2 5 Amino 5 carboxypentyl amino pentanedioic acid 1 IdentifiersCAS Number 997 68 2 N3D model JSmol Interactive image3DMet B01246ChEBI CHEBI 16927 YChemSpider 141086 YDrugBank DB04207 YKEGG C00449 NMeSH saccharopinePubChem CID 160556UNII WBQ73O8W32 NInChI 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 NKey ZDGJAHTZVHVLOT UHFFFAOYSA N NSMILES NC CCCCNC CCC O O C O O C O OPropertiesChemical formula C 11H 20N 2O 6Molar mass 276 289 g mol 1Related compoundsRelated alkanoic acids 4 g Glutamylamino butanoic acidHypusineRelated compounds PalmitoylethanolamideExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Reaction 2 Pathology 3 History 4 See also 5 ReferencesReaction editThe reactions involved catalysed by saccharopine dehydrogenases are lysine alpha ketoglutarate saccharopine glutamate 2 aminoadipate 6 semialdehydePathology editSaccharopinuria 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 editSaccharopine was first isolated in 1961 from yeasts Saccharomyces hence the name by Darling and Larsen 2 See also editOpinesReferences edit 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 Retrieved from https en wikipedia org w index php title Saccharopine amp oldid 1117099027, wikipedia, wiki, book, books, library,

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