Radiation Chemistry of Carbohydrates, IX γ-Radiolysis of N-Acetyl-glucosamine in Aqueous Solution

Abstract

The γ-radiolysis of N-acetyl-glucosamine in deoxygenated (N2O saturated) and oxygenated (N2O/O2 saturated) solutions has been investigated. Eleven products have been characterised and their G-values estimated. Deoxygenated conditions: The principal products identified are 1-acetamido-1,3-dideoxy-2-pentulose (4), 1-acetamido-1-deoxy-2-pentulose (5), 2-acetamido-2,3-dideoxyhexos-4-ulose (6), 2-acetamido-2-deoxy-hexodialdose (7), 2-acetamido-2-deoxy-hexos-5-ulose (8) and 2-acetamido-2-deoxy-gluconic acid (9). Products 1 to 3 contain 3-5 carbon atoms (acetamido group eliminated). Their yields are low. Oxygenated conditions: G values of 5, 7, 8 and 9 are increased, whereas compounds containing a deoxy-keto group (4 and 6) are absent. C-C-bond scission is more important in the presence of oxygen. 2-Acetamido-2-deoxy-tetrodialdose (10) has been identified and a number of products with 5 carbon atoms in the chain retaining the acetamido group (11) have been recognised. Mechanisms for the formation of products are proposed.