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L-Saccharopine (PC000388)

Record Information
Version1.0
Creation date2015-10-09 22:30:23 UTC
Update date2017-01-19 02:36:21 UTC
FoodComEx IDPC000388
FoodDB RecordFDB000461
Chemical Information
NameL-Saccharopine
DescriptionAmino acid from Saccharomyces cerevisiae and Neurospora crassaand is also found in mushrooms and seeds Saccharopine is an intermediate in the degradation of lysine, formed by condensation of lysine and alpha-ketoglutarate. The saccharopine pathway is the main route for lysine degradation in mammal and its first two reactions are catalyzed by enzymatic activities known as lysine-oxoglutarate reductase (LOR) and saccharopine dehydrogenase (SDH), which reside on a single bifunctional polypeptide (EC EC 1.5.1.8, LOR/SDH). The reactions involved by saccharopine dehydrogenases have a very strict substrate specificity for L-lysine, 2-oxoglutarate and NADPH. LOR/SDH has been detected in a number of mammalian tissues, mainly in the liver and kidney, contributing not only to the general nitrogen balance in the organism but also to the controlled conversion of lysine into ketone bodies. A tetrameric form has also been observed in human liver and placenta. LOR activity has also been detected in brain mitochondria during embryonic development, and this opens the question of whether the degradation of lysine has any functional significance during brain development and puts a new focus on the nutritional requirements for lysine in gestation and infancy. Finally, LOR and/or SDH deficiencies seem to be involved in a human autosomic genetic disorder known as familial hyperlysinemia, which is characterized by serious defects in the functioning of the nervous system, and characterized by deficiency in lysine-ketoglutarate reductase, saccharopine dehydrogenase, and saccharopine oxidoreductase activities. 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. (PMID: 463877, 10567240, 10772957, 4809305); 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.
CAS Number997-68-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(S)-N-(5-amino-5-carboxypentyl)-L-Glutamic acidbiospider
Epsilon-N-(L-Glutar-2-yl)-L-lysinebiospider
L-Glutamic acid, N-(5-amino-5-carboxypentyl)-, (S)-biospider
L-N-(5-amino-5-carboxypentyl)-Glutamic acidbiospider
L-saccharopinbiospider
L-saccharopinebiospider
N-(5-amino-5-carboxypentyl)-glutamic acidbiospider
N-(5-amino-5-carboxypentyl)-L-glutamic acidbiospider
N-(5-AMINO-5-CARBOXYPENTYL)GLUTAMIC ACIDbiospider
N-[(5S)-5-amino-5-carboxypentyl]-L-Glutamic acidbiospider
N-[(S)-5-amino-5-Carboxypentyl]-L-glutamateGenerator
N-[(S)-5-Amino-5-carboxypentyl]-L-glutamic acidbiospider
N(6)-(L-1,3-dicarboxypropyl)-L-lysinebiospider
N6-(L-1,3-Dicarboxypropyl)-L-lysinebiospider
Saccharopinbiospider
Saccharopinebiospider
Saccharopine; L-formdb_source
SHRbiospider
Chemical FormulaC11H20N2O6
IUPAC name2-[(5-amino-5-carboxypentyl)amino]pentanedioic acid
InChI IdentifierInChI=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)
InChI KeyZDGJAHTZVHVLOT-UHFFFAOYSA-N
Isomeric SMILESNC(CCCCNC(CCC(O)=O)C(O)=O)C(O)=O
Average Molecular Weight276.2863
Monoisotopic Molecular Weight276.132136382
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointMp 257-259° dec.DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 30 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Toronto Research Chemicals S808340