Hydrolysis of furan and 5-nitrofuran penicillins by penicillinase Bacillus licheniformis

The enzymatic hydrolysis of various furan and 5-nitrofuran penicillins by penicillinaseBacillus licheniformis 749/c was investigated. The effect of various side-chain structural groupings on the rate of inactivation of these compounds was studied. The introduction of bulky substituents in the ortho or positions to the amide group and lengthening the side chain or increasing its degree of unsaturation sharply decrease the catalytic action of penicillinase and, consequently, the rate of cleavage of the-lactam ring of the antibiotic. The majority of the furan and 5-nitrofuran penicillins surpass benzylpenicillin in resistance to the enzyme but are inferior to methicillin and oxacillin.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 295–298, March, 1971