Allysine Explained

Allysine should not be confused with Allicin.

Allysine is a derivative of lysine that features a formyl group in place of the terminal amine. The free amino acid does not exist, but the allysine residue does. It is produced by aerobic oxidation of lysine residues by the enzyme lysyl oxidase. The transformation is an example of a post-translational modification. The semialdehyde form exists in equilibrium with a cyclic derivative.^[1]

Allysine is involved in the production of elastin and collagen.^[2] Increased allysine concentration in tissues has been correlated to the presence of fibrosis.^[3]

Allysine residues react with sodium 2-naphthol-6-sulfonate to produce a fluorescent bis-naphtol-allysine product.^[4] In another assay, allysine-containing proteins are reduced with sodium borohydride to give a peptide containing the 6-hydroxynorleucine (6-hydroxy-2-aminocaproic acid) residue, which (unlike allysine) is stable to proteolysis.^[1]

Further reading

• Luna C, Estévez M . Formation of allysine in β-lactoglobulin and myofibrillar proteins by glyoxal and methylglyoxal: Impact on water-holding capacity and in vitro digestibility . Food Chemistry . 271 . 87–93 . January 2019 . 30236745 . 10.1016/j.foodchem.2018.07.167 . 52309183 .
• Luna C, Arjona A, Dueñas C, Estevez M . Allysine and α-Aminoadipic Acid as Markers of the Glyco-Oxidative Damage to Human Serum Albumin under Pathological Glucose Concentrations . Antioxidants . 10 . 3 . 474 . March 2021 . 33802856 . 8002732 . 10.3390/antiox10030474 . free .

See also

• Saccharopine

Notes and References

1. 10.1007/s00726-003-0012-1 . Recent Advances in the Analysis of Oxidized Proteins . 2003 . Requena . J. R. . Levine . R. L. . Stadtman . E. R. . Amino Acids . 25 . 3–4 . 221–226 . 14661085 . 28837698 .
2. 10.1146/annurev.bi.53.070184.003441. Cross-Linking in Collagen and Elastin. 1984. Eyre. David R.. Paz. Mercedes A.. Gallop. Paul M.. Annual Review of Biochemistry. 53. 717–748. 6148038.
3. Wahsner J, Désogère P, Abston E, Graham-O'Regan KA, Wang J, Rotile NJ, Schirmer MD, Santos Ferreira DD, Sui J, Fuchs BC, Lanuti M, Caravan P . 6 . ⁶⁸Ga-NODAGA-Indole: An Allysine-Reactive Positron Emission Tomography Probe for Molecular Imaging of Pulmonary Fibrogenesis . Journal of the American Chemical Society . 141 . 14 . 5593–5596 . April 2019 . 30908032 . 6494104 . 10.1021/jacs.8b12342 .
4. Waghorn PA, Oliveira BL, Jones CM, Tager AM, Caravan P . High sensitivity HPLC method for determination of the allysine concentration in tissue by use of a naphthol derivative . Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences . 1064 . 7–13 . October 2017 . 28886479 . 5662445 . 10.1016/j.jchromb.2017.08.032 .