Abstract
The reaction between formaldehyde and acetamide which affords a model compound for an amino acid having an amide group was analyzed to investigate the role of formaldehyde as a cross-linking reagent. One of the products was isolated by Sephadex G-10 column chromatography and was identified as N-hydroxymethyl acetamide (FA) by NMR spectro-metry and mass spectrometry. Another product, which could not be isolated, was estimated to be N, N-dihydroxymethyl acetamide (F2A) by kinetic analysis and mass spectrometry. The formation of N, N'-methylene diacetamide was not observed. The mechanism of the reaction between formaldehyde and acetamide was estimated by the kinetic analyses of NMR data, and the rate constants were calculated from the data by the optimization method with a digital computer, On the other hand, formaldehyde cross-linked product was obtained in the reaction of formaldehyde with acetamide and alanine, Its decomposing reaction was analyzed with an NMR spectrometer to study the stability of the formaldehyde cross-linked product. The degradation was dominantly initiated with the release of acetamide.
Consequently, it was estimated that the C-N bond between formaldehyde and amide is so labile that amide-bound formaldehyde does not react further with amides or amines, and that the amide-formaldehyde-amine condensation product is unstable and easily decomposes by releasing the amide.
