SYNTHESES AND ANTIBACTERIAL ACTIVITIES OF PENICILLINS FROM (+)- AND (-)-a-AMINO- 4-ISOTHIAZOLYLACETIC ACIDS
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- RAAP R.
- R & L Molecular Research Ltd.
書誌事項
- 公開日
- 1971
- 資源種別
- journal article
- DOI
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- 10.7164/antibiotics.24.695
- 公開者
- 公益財団法人 日本感染症医薬品協会
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説明
α-Amino-4-isothiazolylacetic acid has been prepared by reaction of α-bromo-4-isothiazalylacetic acid with ammonium hydroxide and by catalytic hydrogenation of α-azido-4-isothiazolylacetic acid. The α-azido acid has been resolved into its two optical isomers from which the optically active amino acids were prepared. The absolute configurations of these amino acids are tentatively assigned. The dextrorotatory isomer can also be prepared directly by resolution of the racemic amino acid with d-camphor-10-sulfonic acid. From the optically active amino acids the penicillins were synthesized by the activated ester method using the p-nitrocarbobenzoxy protecting group. Some MIC and CD50 values against Gram-positive and Gram-negative bacteria are given. The introduction of an α-amino group into 4-isothiazolylmethylpenicillin produces only a minimal effect in the Gram-negative activity.
収録刊行物
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- The Journal of Antibiotics
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The Journal of Antibiotics 24 (10), 695-703, 1971
公益財団法人 日本感染症医薬品協会
