What is N-acetylglucosamine?

From ChitosanWiki
Jump to: navigation, search

N-Acetylglucosamine (official abbreviation GlcNAc, official symbol blue square) is the monomeric building block of chitin (and together with glucosamine one of the two monomeric building blocks of chitosans) where neighboring units are linked via β-1,4-glycosidic bonds. Its systematic name is 2-acetamido-2-deoxy-D-glucopyranose, indicating that it is a derivative of glucose (the most common monomeric or simple sugar) where the hydroxyl (-OH) group at the ring carbon 2 is replaced by an acetylated amino group (-NHCOCH3). GlcNAc can be produced from chitin by full depolymerization, either using mild acid hydrolysis (which however, unless performed very carefully, will lead to a partial loss of the acetyl group, yielding a mixture of GlcNAc and glucosamine) or enzymatically using chitinase in combination with N-acetylglucosaminidase. An alternative but expensive and difficult route would be the chemical N-acetylation of glucosamine which however can easily lead to concomitant and unwanted O-acetylation. Today, there is an efficient biotechnological process to produce GlcNAc from maize starch using recombinant bacteria. GlcNAc can be used as a potentially more efficient substitute for glucosamine in the treatment of arthritis.