D-Amino acids in aged proteins: Analysis and biological relevance

Homochirality is essential for life. L-Amino acids are exclusively used as substrates for the polymerization and formation of peptides and proteins in living systems. However, D-amino acids, which are enantiomers of L-amino acids, were recently detected in various living organisms in the form of free D-amino acids and D-amino acid residues in peptides and proteins. In particular, D-aspartyl (Asp) residues have been detected in various proteins from diverse tissues of elderly individuals. Here, we describe three important aspects of our research: (i) a method for detecting D-beta-Asp at specific sites in particular proteins, (ii) a likely spontaneous mechanism by which Asp residues in proteins invert and isomerize to the D-beta-form with age under physiological conditions, (iii) a discussion of factors that favor such a reaction. (C) 2011 Elsevier B.V. All rights reserved.