4739. Homoserine

Nomenclature

CAS number: 672-15-1
2-Amino-4-hydroxybutanoic acid; 2-amino-4-hydroxybutyric acid; α-amino-γ-hydroxy-n-butyric acid.
C4H9NO3; mol wt 119.12.
C 40.33%, H 7.62%, N 11.76%, O 40.29%.

Description and references

Principal free amino acid occurring in pea plants: A. I. Virtanen, Acta Chem. Scand. 7, 1423 (1953); J.A. Bakhuis, Nature 180, 713 (1957). Prepn: Fischer, Blumenthal, Ber. 40, 106 (1907); Armstrong J. Am. Chem. Soc. 70, 1756 (1948); Birnbaum, Greenstein, Arch. Biochem. Biophys. 42, 212 (1953); M. Frankel, Y. Knobler, J. Am. Chem. Soc. 80, 3147 (1958). Review of homoserine production by fermentation: T. Nara in Microbial Prod. Amino Acids, K. Yamada, Ed. (Wiley, New York, 1972) pp 417-434.

Chemical structure

Derivative

l-Homoserine.

Properties

Flat prisms from 90% alc. Dec 203°. [M]D +21.8° (5N HCl), [M]D +14.3° (glacial acetic acid). [α]D26 8.8° (c = 5 in H2O); [α]D26 +18.3° (c = 2 in 2N HCl). On standing for 8 hrs at 26° the [α]D of the HCl soln decreases to nearly zero as the corresponding levorotatory-γ-butyrolactone is formed.

Derivative

l-Homoserine γ-lactone monohydrochloride.

Properties

Prepd by refluxing l-homoserine with 2N HCl for 2 hrs, crystals, [α]D26 27.0° (c = 5).

Derivative

d-Homoserine.

Properties

Crystals, dec 203°. [α]D26 +8.8° (c = 5).

Derivative

dl-Homoserine.

Properties

Crystals from dil ethanol, dec 186-187°.