Mechanism of Crosslinking of Proteins by Glutaraldehyde I: Reaction with Model Compounds

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Abstract
3H-Glycine and 6-aminohexanoic acid were used as model amine compounds and reacted with glutaraldehyde. Based on the spectral characteristics and the molecular weights obtained from the reaction products, it is concluded that glutaraldehyde can modify amines to form an intermediate which absorbs at 300 nm and has a molecular weight of about 200. In the presence of excess glutaraldehyde, this intermediate is quickly converted to a much larger intermediate which absorb strongly at 265 nm. The larger intermediates are finally altered to yield a strong absorption peak at 325 nm with no apparent change in the molecular weight. These results suggest that a process of polymerization is induced by the initial reaction of glutaraldehyde with amines. The glutaraldehyde-polymer amine complex is self-limiting in size and can undergo internal rearrangement to become chemically inert.