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Identification
YMDB IDYMDB00019
NameSaccharopine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSaccharopine is an intermediate in the biosynthesis of lysine and glutamate in yeast. It is produced from alpha-aminoadipic acid in the alpha-aminoadipic acid pathway. It was first isolated in 1961 from Saccharomyces, hence the name, by Darling and Larsen.[Wikipedia]
Structure
Thumb
Synonyms
  • (S)-N-(5-amino-5-carboxypentyl)-L-Glutamic acid
  • Epsilon-N-(L-Glutar-2-yl)-L-lysine
  • L-N-(5-amino-5-carboxypentyl)-Glutamic acid
  • L-Saccharopin
  • L-Saccharopine
  • N-(5-amino-5-carboxypentyl)-glutamic acid
  • N-(5-amino-5-carboxypentyl)-L-glutamic acid
  • N-[(5S)-5-amino-5-carboxypentyl]-L-Glutamic acid
  • N-[(S)-5-amino-5-Carboxypentyl]-L-glutamate
  • N-[(S)-5-amino-5-Carboxypentyl]-L-glutamic acid
  • N(6)-(L-1,3-dicarboxypropyl)-L-lysine
  • N6-(L-1,3-Dicarboxypropyl)-L-lysine
  • Saccharopin
CAS number997-68-2
WeightAverage: 276.2863
Monoisotopic: 276.132136382
InChI KeyZDGJAHTZVHVLOT-YUMQZZPRSA-N
InChIInChI=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)/t7-,8-/m0/s1
IUPAC Name(2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid
Traditional IUPAC Namesaccharopine
Chemical FormulaC11H20N2O6
SMILES[H]OC(=O)C([H])([H])C([H])([H])[C@]([H])(N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(N([H])[H])C(=O)O[H])C(=O)O[H]
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
  • L-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 Descriptors
Physical Properties
StateSolid
Charge0
Melting point247-250 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.25 g/LALOGPS
logP-2.8ALOGPS
logP-5.4ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.44ChemAxon
pKa (Strongest Basic)10.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149.95 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity63.95 m³·mol⁻¹ChemAxon
Polarizability28.14 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
lysine metabolismPW002420 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Lysine biosynthesisec00300 Map00300
Lysine degradationec00310 Map00310
SMPDB Reactions
Allysine + NADPH + L-Glutamic acid + hydronwater + NADP + Saccharopine
Saccharopine + NAD + waterNADH + hydron + Oxoglutaric acid + L-Lysine
KEGG Reactions
NAD + water + SaccharopineNADH + Oxoglutaric acid + hydron + L-Lysine
L-Allysine + L-Glutamic acid + NADPH + hydronNADP + water + Saccharopine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Xu, H., West, A. H., Cook, P. F. (2006). "Overall kinetic mechanism of saccharopine dehydrogenase from Saccharomyces cerevisiae." Biochemistry 45:12156-12166.17002315
  • Saunders, P. P., Broquist, H. P. (1966). "Saccharopine, an intermediate of the aminoadipic acid pathway of lysine biosynthesis. IV. Saccharopine dehydrogenase." J Biol Chem 241:3435-3440.4287986
  • Ramos, F., Dubois, E., Pierard, A. (1988). "Control of enzyme synthesis in the lysine biosynthetic pathway of Saccharomyces cerevisiae. Evidence for a regulatory role of gene LYS14." Eur J Biochem 171:171-176.3123231
  • Bhattacharjee, J. K. (1985). "alpha-Aminoadipate pathway for the biosynthesis of lysine in lower eukaryotes." Crit Rev Microbiol 12:131-151.3928261
Synthesis Reference:Burkard, Ulrike; Walther, Ingrid; Effenberger, Franz. Amino acids. 6. Investigations on the synthesis of L-saccharopin. Liebigs Annalen der Chemie (1986), (6), 1030-43.
External Links:
ResourceLink
CHEBI ID16927
HMDB IDHMDB00279
Pubchem Compound ID160556
Kegg IDC00449
ChemSpider ID141086
FOODB IDFDB000461
WikipediaSaccharopine
BioCyc IDSACCHAROPINE

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NAD(+)-dependent cleavage of saccharopine to L-lysine and 2-oxoglutarate
Gene Name:
LYS1
Uniprot ID:
P38998
Molecular weight:
41464.39844
Reactions
N(6)-(L-1,3-dicarboxypropyl)-L-lysine + NAD(+) + H(2)O → L-lysine + 2-oxoglutarate + NADH.
General function:
Involved in binding
Specific function:
N(6)-(L-1,3-dicarboxypropyl)-L-lysine + NADP(+) + H(2)O = L-glutamate + L-2-aminoadipate 6-semialdehyde + NADPH
Gene Name:
LYS9
Uniprot ID:
P38999
Molecular weight:
48917.30078
Reactions
N(6)-(L-1,3-dicarboxypropyl)-L-lysine + NADP(+) + H(2)O → L-glutamate + L-2-aminoadipate 6-semialdehyde + NADPH.