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MetaCyc Compound: D-lysine

Synonyms: D-2,6-diaminohexanoic acid

Superclasses: an amino acid or its derivative an amino acid a D-amino acid

Chemical Formula: C6H15N2O2

Molecular Weight: 147.2 Daltons

Monoisotopic Molecular Weight: 146.105527704 Daltons

D-lysine compound structure

SMILES: C([N+])CCCC([N+])C([O-])=O

InChI: InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/p+1/t5-/m1/s1

InChIKey: InChIKey=KDXKERNSBIXSRK-RXMQYKEDSA-O

Unification Links: CAS:923-27-3 , ChEBI:32557 , ChemSpider:4574333 , HMDB:HMDB03405 , KEGG:C00739 , PubChem:5460922

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 69.714745 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

L-lysine degradation V :
D-lysine + oxygen + H2O → 2-keto-6-aminocaproate + ammonium + hydrogen peroxide

Not in pathways:
UDP-N-acetyl-α-D-muramoyl-L-alanyl-D-glutamate + D-lysine + ATP → N6-(UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl)-D-lysine + ADP + phosphate + H+

Not in pathways:
a D-amino acid[in] + an electron-transfer quinone[membrane] + H2O[in] → a 2-oxo carboxylate[in] + ammonium[in] + an electron-transfer quinol[membrane]
a D-amino acid + oxygen + H2O → ammonium + hydrogen peroxide + a 2-oxo carboxylate

Reactions known to produce the compound:

L-lysine degradation V :
L-lysine → D-lysine

Not in pathways:
a peptide with an N-terminal D-amino acid + H2O → a peptide + a D-amino acid + H+
a D-aminoacyl-[tRNA] + H2O → a D-amino acid + an uncharged tRNA + 2 H+

In Reactions of unknown directionality:

Not in pathways:
D-lysine = 2,5-diaminohexanoate

Not in pathways:
acetyl-CoA + a D-amino acid = an N-acetyl-D-amino acid + coenzyme A + H+
an N-carbamoyl D-amino acid + H+ + H2O = a D-amino acid + ammonium + CO2
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an L-amino acid = a D-amino acid

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

In Redox half-reactions:
a 2-oxo carboxylate[in] + ammonium[in] + 2 H+[in] + 2 e-[membrane]a D-amino acid[in] + H2O[in]

This compound has been characterized as an alternative substrate of the following enzymes: lysine 5,6-aminomutase


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Sun Apr 26, 2015, biocyc12.