DL‐homoserinehydroxamic Acid, DL‐homo‐cystinedihydroxamic Acid, and Derivatives by Hydroxylaminolysis of γ‐Hydroxy‐ and γ‐Thio‐Lactones

Y. Knobler, S. Bittner, M. Frankel

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The reaction of α‐amino‐, α‐carbamoylamino‐, α‐benzamido‐, and α‐benzyloxycarbonyl‐amino‐γ‐butyrolactone with hydroxylamine led to the formation of DL‐homoserinehydroxamic acid and α‐N‐acyl derivatives. α‐N‐Benzoyl‐DL‐homoserine‐N‐methyl‐hydroxamic acid and O‐benzylhydroxamic acid ester were prepared by reacting α‐benzamido‐γ‐butyrolactone with N‐methylhydroxylamine and with O‐benzylhydroxylamine, respectively. Hydroxyl‐aminolysis of DL‐homocysteinethiolactone and of N‐acyl‐DL‐homocysteinethiolactones gave homocystinedihydroxamic acid and N,N′‐disubstituted derivatives. Relative reactivities of O‐ and S‐lactones were compared.

Original languageEnglish
Pages (from-to)639-645
Number of pages7
JournalIsrael Journal of Chemistry
Volume8
Issue number4
DOIs
StatePublished - 1 Jan 1970
Externally publishedYes

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