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词条 Saccharopine
释义

  1. Reaction

  2. Pathology

  3. History

  4. See also

  5. References

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| ImageFile = Saccharopine.PNG
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageName = Stereo, skeletal formula of saccharopine ((2S)-2-{[(5S)-5-aminopentyl]amino})
| IUPACName = 2-[(5-Amino-5-carboxypentyl)amino]pentanedioic acid[1]
|Section1={{Chembox Identifiers
| CASNo = 997-68-2
| CASNo_Ref = {{cascite|changed|??}}
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = WBQ73O8W32
| PubChem = 160556
| ChemSpiderID = 141086
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| DrugBank = DB04207
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG = C00449
| KEGG_Ref = {{keggcite|changed|kegg}}
| MeSHName = saccharopine
| ChEBI = 16927
| ChEBI_Ref = {{ebicite|correct|EBI}}
| 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 = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ZDGJAHTZVHVLOT-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
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|Section2={{Chembox Properties
| C=11 | H=20 | N=2 | O=6
}}
|Section3={{Chembox Related
| OtherFunction_label = alkanoic acids
| OtherFunction = {{unbulleted list|4-(γ-Glutamylamino)butanoic acid|Hypusine}}
| OtherCompounds = Palmitoylethanolamide
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}}

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.

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.[2]

See also

  • Opines

References

1. ^{{cite web|title=N-(5-AMINO-5-CARBOXYPENTYL)GLUTAMIC ACID - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1087&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=11 July 2012|location=USA|date=23 June 2005|at=Identification}}
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).
{{amino acid metabolism intermediates}}

3 : Amino acids|Tricarboxylic acids|Dipeptides

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