By Edwin H. Flynn
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Additional info for Cephalosporins and Penicillins. Chemistry and Biology
Because the reversibility of this reaction and its biosynthetic implica tions will be covered in Chapter 9, little reference will be made to this property in this section. B. Isolation and Distribution of Microorganisms which Produce Acylase Activity Although acylase-producing microorganisms may be isolated by conven tional techniques, Kameda et al. (1961) reported a medium for selecting microorganisms with acylase activity. This medium contained benzylpenicillin as a sole carbon source and inorganic salts.
It was separated from the aqueous phase by ethyl acetate extraction at neutral pH. The yield was 66%. In a separate step, the benzhydryl ester (26c) was hydrolyzed at room temperature, using anhydrous trifluoroacetic acid with anisole. 5 in 91 % yield. The same workers described another cleavage of JV5J/V-phthaloyl cephalosporin C dibenzhydryl ester (25g). A 10% solution of phosphorus pentachloride in méthylène chloride was used in place of phosphorus oxychloride. After a half-hour at 20°, methanol was added.
C02H H3NX o2c x ^ CH(CH 2 ) 3 N (28) L X C0 2 H H3NX / CH(CH 2 ) 3 ö2c NC02H x (29) 3. DERIVATIVES Reaction of penicillin N with 1,2,4-fluorodinitrobenzene, benzoyl chloride, benzyloxycarbonyl chloride, phenylisocyanate, and acetic anhydride, respec tively, yielded derivatives which no longer contained the free amino group of the α-aminoadipyl side chain of the parent compound. In contrast to penicillin 1. 1 % ofthat against the former. Changes in relative antibacterial activity which were qualitatively similar were found in the other cases although they became progressively smaller with the Af-benzoyl, N-benzyloxycarbonyl, phenylthiocarbamyl, and N-acetyl derivatives respec tively (Newton and Abraham, 1954).