Glucosamine is an amino sugar, conventionally 2-amino-2-deoxy-D-glucose. Relative to the open-chain glucose reference structure, its carbon-2 hydroxy group is replaced by an amino group, with the corresponding stereochemical arrangement retained.[ref]
Nomenclature of Carbohydrates (Recommendations 1996) by Alan D. McNaught. Section 2-Carb-14: D-glucosamine and amino-deoxy naming
Replacing by removes one oxygen and adds one nitrogen and one hydrogen. Thus the neutral free base has molecular formula , compared with for glucose. This is structural bookkeeping, not a claim that every preparation is made by one replacement reaction.
N-acetylglucosamine further modifies that nitrogen. Distinguishing the two names matters when identifying a polysaccharide's building blocks: an acetyl group changes chemical identity even though the six-carbon framework remains recognizable.[ref]
Nomenclature of Carbohydrates (Recommendations 1996) by Alan D. McNaught. Section 2-Carb-25: amino-sugar nitrogen substitution
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