H

H —N C

Desmosine

Figure 4 Formation of allysine and structure of desmosine.

Proteins within living systems can also be damaged by covalent binding to other molecules (usually reactive biochemicals) to form adducts, thereby rendering the protein inoperative or immunogenic. Adducts can be formed by the reaction of an aldehyde function with a receptive nucleophilic centre in the protein, particularly the e-amino groups on lysine residues but also the a-amino terminus, the thiol groups on cysteine residues, the imidazole groups on histidine residues, and the phenolic groups on tyrosine residues. The aldehydes that may be involved in adduct formation include malondialdehyde and 4-hydroxy-2-nonenal, which are produced by free radical damage to polyunsaturated fatty acids in cell membranes, and acetaldehyde, which is produced when alcohol is metabolized. Adduct formation may play a role in the pathological processes leading to diseases such as alcoholic cirrhosis and coronary heart disease.

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