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Chemical Compound Review

allysine     2-amino-6-oxo-hexanoic acid

Synonyms: CHEBI:17027, HMDB01263, FT-0673438, AC1L18PV, UNII-425I4Y24YZ, ...
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Disease relevance of allysine


Psychiatry related information on allysine

  • A time study indicated that allysine levels increased primarily after the bulk of Schiff base synthesis [2].

High impact information on allysine

  • It was subsequently shown that the apparent deficiency in lysyl residues was due, at least in part, to the presence of unusually high levels of allysine , a cross-link precursor formed from peptide-bound lysine under the catalytic action of lysyl oxidase [3].
  • The elastin incubated with ammonium chloride showed that DESP and IDP levels increased as the allysine content decreased [4].
  • Acid hydrolysis followed by amino acid analysis of envelopes either reduced with NaB[3H]4 or labeled with [14C]lysine and reduced with NaBH4 yielded allysine and two labeled fragments with elution profiles and molecular weights (250 and 330) consistent with Schiff base products derived at least in part from allysine [5].
  • Oxidative deamination of the epsilon-amino group of lysyl residues to form allysine is the initial reaction in the cross-linking of collagen and elastin in vertebrates [5].
  • Several enzymes of the lysine pathway of Saccharomyces cerevisiae were found to respond to an induction mechanism mediated by the product of gene LYS14 in the presence of 2-aminoadipate semialdehyde, an intermediate of this pathway [6].

Chemical compound and disease context of allysine


Anatomical context of allysine


Gene context of allysine

  • The leaky auxotrophic behaviour of lys14 mutants is explained by the low basal level of expression of LYS9, the structural gene of this enzyme, in the absence of induction by 2-aminoadipate semialdehyde [6].
  • The allysine content in rat aorta elastin dramatically increased from 1 week to 2 weeks of age [9].


  1. Lysyl-derived aldehydes in outer membrane proteins of Escherichia coli. Diedrich, D.L., Schnaitman, C.A. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  2. Collagen cross-linking. Effect of D-penicillamine on cross-linking in vitro. Siegel, R.C. J. Biol. Chem. (1977) [Pubmed]
  3. An unusual pattern of peptide-bound lysine metabolism in collagen from an infant with lethal perinatal osteogenesis imperfecta. Petrovic, O.M., Miller, E.J. J. Clin. Invest. (1984) [Pubmed]
  4. Two new elastin cross-links having pyridine skeleton. Implication of ammonia in elastin cross-linking in vivo. Umeda, H., Takeuchi, M., Suyama, K. J. Biol. Chem. (2001) [Pubmed]
  5. Oxidative deamination of epsilon-aminolysine residues and formation of Schiff base cross-linkages in cell envelopes of Escherichia coli. Mirelman, D., Siegel, R.C. J. Biol. Chem. (1979) [Pubmed]
  6. Control of enzyme synthesis in the lysine biosynthetic pathway of Saccharomyces cerevisiae. Evidence for a regulatory role of gene LYS14. Ramos, F., Dubois, E., Piérard, A. Eur. J. Biochem. (1988) [Pubmed]
  7. Enzymatic synthesis of chiral intermediates for Omapatrilat, an antihypertensive drug. Patel, R.N. Biomol. Eng. (2001) [Pubmed]
  8. Lysine-derived cross-links in the egg shell membrane. Crombie, G., Snider, R., Faris, B., Franzblau, C. Biochim. Biophys. Acta (1981) [Pubmed]
  9. High-performance liquid chromatographic quantification of allysine as bis-p-cresol derivative in elastin. Umeda, H., Kawamorita, K., Suyama, K. Amino Acids (2001) [Pubmed]
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