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In addition to the protonation of the amide groups and the subsequent disruption of the hydrogen-bonding pattern, the imine groups also can be protonated, and this, in turn, can cause syn - anti changes around the C=N bond. However, the changes in the chiroptical properties of L,L-PIAA and L-PIGA induced by acid were irreversible upon neutralization of the solution with a base, and similar, albeit less pronounced, changes in the CD spectra were also found for L,L-PIAA and L,D-PIAA with increasing temperature (see the text). This suggests that these are not likely the result of the protonation of the imines (see refs. 31 and 32). It has been found recently that the acid-induced changes in the chiroptical properties of L,D-PIAA can be reversed completely by titration with a base (see ref. 33).
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