Aliphatic linear omega-aminocarbonyl-aminocarboxylic acid prepn. - by esterification of omega-hydroxy-carbonyl-aminocarboxylic acid with lower alkanol, aminolysis and hydrolysis of amide with hydrolase

摘要

In prepn. of aliphatic, straight-chain omega-aminocarbonyl-amino carboxylic acids (I), (a) an omega-hydroxycarbonyl amino carboxylic acid is dissolved in a lower aliphatic alcohol, heated with addn. of a mineral acid, and allowed to react, giving the omega-alkoxycarbonyl amino carboxylic acid (II) and an ester (III) of (II), (b) the mixt. is treated with NH4OH, giving a mixt. mainly of (I) and an amide (IV) of (I), (c) (I) is sepd. from the reaction mixt. and (IV) is hydrolysed in aq. soln. with addn. of a hydrolase, forming (I), and (d) the (I) is isolated from the reaction mixt. and is combined with the (I) previously sepd. In (a) the acid is pref. aspartic or glutamic acid. The alcohol is 1-6C, and reaction is under reflux, with addn. of H2SO4, HCl or HNO3. In (b), 3-15 mols of NH4OH are used w.r.t. 1 mol of ester gp. In (c) prepn. of (I) from the corresp. (IV) comprises dissolving (IV) in water or a buffer soln. and treating with a hydrolase, pref. a protease, esp. bromelaine. (I) is isolated from each mixt. chromatographically or crystallographically. USE/ADVANTAGE - (I) are obtd. in good yield in a simple process, from easily available free amino-alpha,omega-dicarboxylic acids, without the need to protect the amino gp. Pure enantiomers of mono-amides of aminoacids with 2 COOH gps. e.g. glutamine or asparagine, are used in medicines and foods.