Studies of the mechanism of the periodic acid-Schiff histochemical reaction for glycogen using infrared spectroscopy and model chemical compounds.

It has been proposed in the literature that Schiffs reagent reacts with aldehydes to form one of the following types of compounds: alkylsulfonic acids, N-sulfinic acid derivatives, or Schiff bases. Model compounds whose structures are consistent with those proposed in the literature have been synthesized and subjected to infrared analysis. Also, actual products of Schiff reagent reactions with various aldehydes have been isolated and examined using infrared spectroscopy. Comparison of the spectra of the model compounds with those of Schiff-aldehyde reaction products yielded the following conclusions: 1. The reaction of simple organic aldehydes with Schiff's reagent produces an alkylsulfonate-type reaction product. 2. The reaction of periodate-oxidized glycogen with Schiff's reagent probably involves the formation of an alklsulfonate-type compound. 3. The product of the Schiff-aldehyde reaction exists as neither an N-sulfinic acid nor a Schiff base derivative of the fuchsin molecule.