Effect of Heavy Water on Three High Producing Strains of Penicillium chrysogenum

Mohammed, Kasheed; Nona, Daniel A.; Blake, Martin I.

doi:10.1002/jps.2600590335

Cited by 3 publications

(1 citation statement)

References 6 publications

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“…As part of a fluorescence immunoassay for phencyclidine (l-(l-phenylcyclohexyl)piperidine (1), we required derivatives of 1 which would be sufficiently nucleophilic that they could be covalently coupled to appropriate fluorescent dyes and proteins. Although many phencyclidine analogues have been synthesized,1 the general procedure used to make most of them precludes incorporation of functional groups, such as primary amines, which contain acidic protons.…”

Section: Methodsmentioning

confidence: 99%

Preparation of 6-deuteriopenicillins

Claes¹,

Roets²,

Herdewijn³

et al. 1981

J. Org. Chem.

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When penicillin (S)-S-oxide esters are treated with triethylamine and acetonitrile containing DzO, both epimerization and deuteration at the 6-position occurs. This reaction is found to be a convenient method for the preparation of 6-deuteriopenicillins. 6-Deuteriobenzylpenicillin (S)-S-oxide benzyl ester (containing more than 95% D in the 6-position) was obtained from the (S)-S-oxide of penicillin G benzyl ester. Deoxygenation of the sulfoxide followed by catalytic debenzylation gave penicillin G deuterated in the 6-position. A kinetic study of deuterium incorporation and epimerization at C-6 was carried out for the (S)-S-oxide of penicillin V benzyl ester and for its 6-epimer. Deuteration was found to be faster than epimerization when the sulfoxide with the natural configuration was used as starting material. In the experiment starting with the 6-epimer, epimerization is faster than deuteration. A revised mechanism for the epimerization and deuteration of penicillin S-oxide esters is proposed.

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Section: Methodsmentioning

confidence: 99%