DL-cyclocanaline (cyclohomoserine) and related compounds

M. Frankel, Y. Knobler, E. Bonni, S. Bittner, G. Zvilichovsky

Research output: Contribution to journalArticlepeer-review

10 Scopus citations


DL-Cyclocanaline (4-aminotetrahydro-1,2-oxazin-3-one) hydrochloride, the higher homologue of the antibiotic cycloserine, has been prepared from canaline (2-amino-4-amino-oxybutyric acid) dihydrochloride. Its chemical and physical properties are reported. α-N-Triphenylmethyl- and α-N-benzoyl-cyclocanaline have been synthesised by N-tritylation of the oxa-lactam and by cyclisation of the α-benzamidocanaline ester derivative, respectively. Derivatives of DL-canaline ester bearing various protecting groups on the amino- and aminooxy-groups were obtained; N-benzyloxycarbonylhydroxylamine was utilised for the introduction of the amino-oxy group.

Original languageEnglish
Pages (from-to)1746-1749
Number of pages4
JournalJournal of the Chemical Society C: Organic Chemistry
Issue number13
StatePublished - 1 Jan 1969
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


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