N-acetyl-β-glucosamine is reducing sugar whereas D-gluconate and GlcN(α1-1α-)Glc are non reducing sugar.
Because it has a free anomeric carbon at position C-1 that can open to the straight-chain form and be oxidized, N-acetyl-β-glucosamine is a reducing sugar. D-gluconate is not a reducing sugar because its anomeric carbon at C-1 is already oxidized to the level of a carboxylic acid. Because it lacks a free anomeric carbon, the disaccharide GlcN(α1-1α-)Glc is not a reducing sugar. This compound's two glucose units' anomeric carbons are linked together by an O-glycosidic bond, preventing them from opening to the straight-chain forms needed for oxidation.
Hence, reducing behavior is decided on basis of free OH group on anomeric carbon.
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