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Encyclopedia Britannica



ASPARAGINE

This article appears in Volume V02, Page 765 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: ARN-AUD
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.
HOOCCHNH2CH2COOC2H5+NH3
= C2H SOH +H000CH NH2CH2CONH2. 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 234235 C. Nitrous acid converts it into malic acid, HOOCCHOHCHZCOOH. 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).


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