Asparagine
ASPARAGINE, C4H3N2O3, 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 1805 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 = C2H5OH + HOOC·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·CH2·COOH. It is laevo-rotatory in aqueous or in alkaline solution, and dextro-rotatory in acid solution (L. Pasteur, Ann. Chim. Phys., 1851 [2], 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 dextro-rotatory 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).
Note - this article incorporates content from Encyclopaedia Britannica, Eleventh Edition, (1910-1911)
