A new 2-substituted thiazolidine-4(R)-carboxylic acid (TCA), 2-glucosamine-TCA (GlcNH(2)Cys), was synthesized with its antioxidative properties, compared with those of 2 other 2-substituted TCAs, 2-gluco-TCA and 2-galacto-TCA. The GlcNH(2)Cys showed antioxidative properties of scavenging reactive free radicals (hydroxyl radical and superoxide anion), preventing macromolecules damage (deoxyribose, protein, and lipid), and was hepatoprotective against acetaminophen-induced liver damage by replenishing sulfhydryl levels, increasing the total antioxidative capacity of the liver, and inhibiting lipid peroxidation. GlcNH(2)Cys is a promising compound to protect against oxidative stress xenobiotics. (c) 2006 Elsevier Inc. All rights reserved.