FACTORS INFLUENCING BY-PRODUCT FORMATION IN THE REACTION OF 1-FLUORO-2,4-DINITROBENZENE WITH AMINO SUGARS AND AMINODEOXYALDITOLS

Article abstract of DOI:10.1016/S0008-6215(00)84575-9

By-product formation, in decreasing order of severity, occured during the reaction of 2-amino-3-O-<1-(S)-carboxyethyl>-2-deoxy-D-glucose (muramic acid), 2-amino-2-deoxy-D-glucose, and the corresponding aminodeoxyalditols with 1-fluoro-2,4-dinitrobenzene.The fine balance between incomplete derivatisation at pH 8.5 and the formation of by-product at pH 9.5 was best achieved by reaction in carbonate buffer (pH 9.0) in aqueous ethanol.Higher pH values or temperatures, and especially the use of tertiary amine buffers and dipolar aprotic solvents, increased by-products production.The implications for quantitative analysis of amino sugars are discussed.