6706. Norleucine

Nomenclature

CAS number: 327-57-1
l-Norleucine; α-aminocaproic acid; (S)-2-aminohexanoic acid; glycoleucine; caprine.
C6H13NO2; mol wt 131.17.
C 54.94%, H 9.99%, N 10.68%, O 24.39%.

Description and references

An amino acid classified as nonessential with respect to its growth effect in rats. Several syntheses; prepn from α-bromo-n-caproic acid by action of 25% ammonia at 50-55°: Marvel, du Vigneaud, Org. Synth. 4, 3 (1925).

Chemical structure

Properties

Slightly sweet, shiny leaflets from water. mp 301° (partial decompn). Sublimes partially at 275-280°. [M]D +32.1° (5N HCl); +47.9° (glacial acetic acid). [α]D20 +21.3° (c = 4.25 in 6N HCl); +6.26° (c = 0.70 in water).

Derivative

dl-Form.

Nomenclature

CAS number: 616-06-8

Properties

Lustrous leaflets from water. d 1.172. Dec 327°. pK1 2.39; pK2 9.76. Soly in water: 11.49 g/l at 25°, 17.27 g/l at 50°, 28.61 g/l at 75°, 52.0 g/l at 100°. Sparingly sol in alcohol: 0.42 g/100 g at 25°. Sol in acids.

Derivative

d(-)-Form.

Nomenclature

CAS number: 327-56-0

Properties

Bitter, shiny leaflets from water. mp 301° (partial decompn). Sublimes partially at 275-280°. [α]D20 -22.4° (c = 4.69 in 6N HCl); -4.49° (c = 0.96 in water).