908. 2-Azetidinecarboxylic Acid

Nomenclature

CAS number: 2517-04-6
C4H7NO2; mol wt 101.10.
C 47.52%, H 6.98%, N 13.85%, O 31.65%.

Description and references

From Convallaria majalis L. (lily-of-the-valley) and Polygonatum officinale Moensh., Liliaceae: Fowden, Biochem. J. 64, 323 (1956); Fowden, Bryant, ibid. 70, 626 (1958). Structure: Virtanen, Angew. Chem. 67, 619 (1955); Fowden, loc. cit. Biosynthesis: Linko, Acta Chem. Scand. 12, 101 (1958); Fowden, Bryant, Biochem. J. 71, 210 (1959); Fowden, ibid. 71, 643 (1959); Leete, J. Am. Chem. Soc. 86, 3162 (1964). Shows growth-inhibitory activity on cultures of Escherichia coli and on germinating seeds of different species in which it does not normally occur; Fowden, Richmond, Biochim. Biophys. Acta 71, 459 (1963). Acts as a proline analog where a stoichiometric replacement of proline occurred with production of abnormal proteins having impaired biological activity: Peterson, Fowden, Nature 200, 148 (1963).

Chemical structure

Properties

Crystals from 95% hot methanol, discolors at 200° and darkens until 310° when heating stopped. [α]D20 108° (c = 3.6). Unstable to mineral acids. Soluble in cold and hot water. Practically insol in abs ethanol.