2-vinylpenams and process

Details 2-vinylpenams and process 2-vinylpenams and process

1986-04-29

1987-05-19

Trousof, Natalie

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing compound having a 1-thia-4-aza-bicyclo

540312, 540314, 540328, C12P 3700, C07D49942, C07D49946

Patent

active

046668357

ABSTRACT:
6.beta.-(L-.alpha.-Aminoadipoyl)-2.alpha.-vinyl-2.beta.-methylpenam-3-carbo xylic acid is provided in an enzymatic process converting .delta.-(L-.alpha.-aminoadipoyl)-L-cysteinyl-D-.gamma.,.delta.-didehydrois oleucine with isopenicillin N synthetase. The 2.alpha.-vinylpenam product is converted by known methods to the 6.beta.-amino-2.alpha.-vinyl-2.beta.-methylpenam-3-carboxylic acid nucleus and the latter is N-acylated to provide corresponding 6.beta.-acylaminopenams.

REFERENCES:
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patent: 4539149 (1985-09-01), Milner
Pang et al., Biochem. J. (1984), 222, 789-795, "Purification of Isopenicillin N Synthetase".
Baldwin et al., FEBS Letters, 1985, 188, 253-256.
Bartlett et al., J. Org. Chem., 1982, 47, 3933-3941, "Ester-Enolate Claisen Rearrangement of Alpha-Amino Acid Derivatives".
Baldwin et al., J. Chem. Soc., Perkin I, 1981, 2253.
Baldwin et al., J. Chem. Soc., Chem. Commun., 1986, 273-275.
Baldwin et al., J. Chem. Soc., Chem. Commun., 1984, 1211-1214.

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