Mercuric chloride Penicillamine

Robinson, C.J., Balazs, T., and Egorov, I.K., Mercuric chloride-, gold sodium thiomalate-, and D-penicillamine-induced antinuclear antibodies in mice. Toxicol. Appl. Pharmacol., 86, 159, 1986. 

Penicilloic acids (III) react instantly in aqueous solution with mercuric chloride 19d giving penicillamine (VII) and penaldic acid (VI). Penaldic acids decarboxylate rapidly to form the corresponding penilloaldehyde (VIII). This degradation forms the basis for a sensitive analytical method for benzylpenicillin. ... 

D-Penicillamine was found to be identical with the natural penicillamine. When treated with diazomethane (CH2=N =N ), penicillin is converted into its methyl ester and this, on treatment with an aqueous solution of mercuric chloride, gives the methyl ester of pencillamine, thereby proving that the carboxyl group in penicillamine is the carboxyl group present in the penicillin moelcule itself 4. Penilloaldehyde... 

It has been established experimentally that penilloic acid upon hydrolysis with aqueous mercuric chloride yields penicillamine and penilloaldehyde respectively. This type of hydrolysis is characteristic of compounds containing a thiazolidine ring, i.e.,... 

Pusey CD, Bowman C, Morgan A, Weetman AP, Hartley B, Lockwood CM (1990) Kinetics and pathogenicity of autoantibodies induced by mercuric chloride in the Brown Norway rat. Clin Exp Med 81 76-82 Reeves AL (1983) The immunotoxicity of beryllium. In Gibson CG, Hubbard R, Parke DV (eds) Immunotoxicology. Academic, London, p 261 Robinson CJG, Abraham A A, Balazs T (1984) Induction of anti-nuclear antibodies by mercuric chloride in mice. Clin Exp Immunol 58 300-306 Robinson CJG, Balazs T, Egorov IK (1986) Mercuric chloride, gold sodium thio-malate, and D-penicillamine-induced anti-nuclear antibodies in mice. Toxcol Appl Pharmacol 86 159-169... 

Elucidation of the structure of the penicillin nucleus involved extensive degradation studies and X-ray analysis. Reaction of a penicillin under hydrolytic conditions followed by further degradation with mercuric chloride was shown to give D-penicillamine (46) and the penilloaldehyde (47). From this evidence it was concluded that the primary hydrolysis... 

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