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Sample text

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).

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