ASPARAGINE  , C4HsN203, a naturally occurring

base, found in plants belonging to the natural orders Leguminosae and Cruciferae . It occurs in two optically active forms, namely, as laevo-asparagine and dextro-asparagine . Laevo-asparagine was isolated in 18os by L . N . Vauquelin . A . Piutti (Gazz. chim . Ital., 1887, 17, p . 126; 1888, 18, p . 457) synthesized the asparagines from the monomethyl ester of inactive aspartic acid by heating it with alcoholic ammonia . In this way a mixture of the two asparagines was obtained, which were separated by picking out the hemihedral crystals . HOOC•CH•NH2•CH2•COOC2H5+NH3 = C2H SOH +H000•CH• NH2•CH2•CONH2 .

Laevo-asparagine is slightly soluble in

cold water and readily soluble in hot water . It crystallizes in prisms, containing one molecule of water of crystallization, the anhydrous form melting at 234–235° C . Nitrous acid converts it into malic acid, HOOC•CHOH•CHZ•COOH . It is laevo-rotatory in aqueous or in alkaline solution, and dextro-rotatory in acid solution (L . Pasteur, Ann.Chim . Phys., 1851 [21, 31, p . 67) . Dextro-asparagine was first found in 1886 in the shoots of the vetch (Piutti) . It forms rhombic crystals possessing a sweet taste . It is dextrorotatory in aqueous or alkaline solution, and laevo-rotatory in acid solution . Hydrolysis by means of acids or alkalis converts the asparagines into aspartic acid; whilst on heating with water in a sealed tube they are converted into ammonium aspartate . The constitution of the asparagines has been determined by A .

Piutti (Gazz. chim . Ital., 1888, 18, p . 457) .