acid hydrolysis of penicillin mechanism


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PDF Hydrolysis of Penicillin G and Carbenicillin in Pure Water

It is reasonable that the hydrolysis occurred due to the protonation of nitrogen atom of β-lactam ring (acid mechanism) In spite the fact the hydrolysis

  • What is the hydrolysis reaction of penicillin?

    Enzymatic hydrolysis of penicillin G to produce 6-aminopenicillanic acid, key intermediate for the production of semisynthetic β-lactam antibiotics, is one of the most relevant example of industrial implementation of biocatalysts.
    The hydrolysis reaction is traditionally carried out in aqueous buffer at pH 7.5-8.

  • The hydrolysis product, penicilloic acid or cephalosporoic acid, is biologically inactive.
    FIGURE 8.4.

  • Is penicillin destroyed by acids?

    Penicillin G degrades more easily by stomach acid and has less than 30% bioavailability; therefore, it is a parenterally administered drug.
    Because of the short half-life, penicillin G is usually administered in divided doses 4 to 6 hours apart via the intravenous or intramuscular route.

  • How does penicillin degrade in acidic media?

    It is well known that penicillin decomposes in acidic aqueous solution to form both penillic acid (V) and penilloic acid (111) with a maximum yield of the former at pH 2-3 (1).
    It is also known that penicillenic acid (IV) is formed in acid solution and subsequently decomposes relatively rapidly (2).

  • One is the acid catalyzed hydrolysis of the undissociated penicillin molecule to form penilloic acid. The second is rearrangement of the penicillin ion following attack by proton or the kinetically equivalent uncatalyzed reaction of undissociated penicillin to form penicillenic acid which rearranges to penillic acid.
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