2984. 2,3-Diaminopropionic Acid

Nomenclature

CAS number: 515-94-6
3-Aminoalanine; 2,3-diaminopropanoic acid; α,β-diaminopropionic acid.
C3H8N2O2; mol wt 104.11.
C 34.61%, H 7.75%, N 26.91%, O 30.74%.

Description and references

Prepd by treating 2,3-dibromopropionic acid with ammonia: Klebs, Z. Physiol. Chem. 19, 314 (1894); Winterstein, Küng, ibid. 59, 146 (1909); Neuberg, Silbermann, Ber. 37, 341 (1904); Frankland, J. Chem. Soc. 97, 1318 (1910); by treating 2-amino-3-chloropropionic acid with ammonia under pressure: Fisher et al., Ber. 40, 3717 (1907); by the reduction of cyanooximoacetic acid esters: Godefroi, US 2738363 (1956 to Parke, Davis). Configuration: Karrer et al., Helv. Chim. Acta 9, 314 (1926). See also Bergmann, Grafe, Z. Physiol. Chem. 187, 187 (1930).

Chemical structure

Derivative

dl-Form.

Properties

Radially arranged cryst masses. Hygroscopic, also absorbs CO2 from air. Begins to melt at 97°, completely liquid at 110-120°. Sol in water, yielding alkaline solns. Practically insol in alcohol, ether.

Derivative

Hydrochloride.
C3H8N2O2.HCl; mol wt 140.57.
C 25.63%, H 6.45%, N 19.93%, O 22.76%, Cl 25.22%.

Properties

Needles or leaflets, mp 236-237°. One gram dissolves in 12 ml water, practically insol in alcohol.

Derivative

Sulfate hemihydrate.
(C3H8N2O2)2.H2SO4. 1/2 H2O; mol wt 315.30.
C 22.86%, H 6.07%, N 17.77%, O 43.13%, S 10.17%.

Properties

Six-sided leaflets from water, dec 233-234°. One gram dissolves in 31 ml water at 20°.

Derivative

Methyl ester dihydrochloride.
C4H10N2O2.2HCl; mol wt 191.06.
C 25.15%, H 6.33%, N 14.66%, O 16.75%, Cl 37.11%.

Properties

Crystals, dec 170°. Freely sol in water.

Derivative

Ethyl ester dihydrochloride.
C5H12N2O2.2HCl; mol wt 205.08.
C 29.28%, H 6.88%, N 13.66%, O 15.60%, Cl 34.57%.

Properties

Crystals, mp 164.5-165° (some decompn). Freely sol in water.

Derivative

l-Form hydrochloride.
C3H8N2O2.HCl; mol wt 140.57.
C 25.63%, H 6.45%, N 19.93%, O 22.76%, Cl 25.22%.

Properties

Needles from water, [α]D20 +25.0° (c = 5 in 1.0N HCl).

Derivative

d-Form hydrochloride.
C3H8N2O2.HCl; mol wt 140.57.
C 25.63%, H 6.45%, N 19.93%, O 22.76%, Cl 25.22%.

Properties

Needles from water, [α]D20 -25.3° (c = 5 in 1.0N HCl).

Use

The salts as growth inhibitors for microorganisms.