Benzylpenicillenic acid formation

Wagner ES, Davis WW, Gorman M (1969) The reaction of benzylpenicillenic acid with thiol-containing compounds. The formation of a possible penicillin antigenic determinant. J Med Chem 12 438-487... 

Butcher BT, Stanfield MK, Stewart GT, Zemelman R (1971) Antibiotic polymers alpha-amino-benzylpenicillin (ampicillin). Mol Cryst Liq Cryst 12 321 Butler TC, Dudley KH, Johnson D (1972) Chemical studies of potential relevance to penicillin hypersensitivity kinetics of formation and disappearance of benzylpenicillenic acid and its derivatives in solutions of benzylpenicillin. J Pharmacol Exp Ther 181 201 Butterly JM, Fishman L (1972) Jarisch-Herxheimer reaction following penicillin therapy in case of symphilitic aortitis. JAMA 148 370... 

Levine BB (1960 c) Formation of D-penicillamine-cysteine mixed disulphide by reaction of D-benzylpenicilloic acide with cysteine Nature 187 940 Levine BB (1961) Studies on the formation of the penicillin antigen. II. Some reactions of D-benzylpenicillenic acid in aqueous solution at pH 7.5. Arch Biochem Biophys 93 50 Levine BB (1962) N(a-D-penicilloyfamines as univalent hapten inhibitors of antibody-de-pendent allergic reactions to penicillin. J Med Chem 5 1025 Levine BB (1963) Studies on the dimensions of the rabbit anti-benzyl penicilloyl antibody combining sites. J Exp Med 117 161... 

Maggs, John Farrell, Catherine S Lane, Andrew V Stachulski, NeU S French, Dean J Naisbitt, Munir Pirmohamed, B. Kevin Park. Direct evidence for the formation of diastereoisomeric benzylpenicUloyl haptens from benzylpenidllin and benzylpenicillenic acid in patients. J Pharmacol Exp Then 2011 338 841-9. Reprinted with permission from Americtm Society for Pharmacology and Experimental Therapeutics... 

Benzylpenicillenic acid [38] is not formed in acidic solution (pH < 1) where its rate of formation is pH-independent. 

The presence of copper(II) ion has little effect upon the rate of formation of penicillenic acid from benzylpenicillin. Furthermore, the rates of hydrolysis and aminolysis of benzylpenicillenic acid are retarded in the presence of copper(II) ion. Since the observed rates of hydrolysis and aminolysis of penicillin in the presence of copper(II) ion are at least 10 times faster than the rate of formation of penicillenic acid from penicillin these reactions cannot... 

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