802919-55-7Relevant academic research and scientific papers
Exploring the chemistry of penicillin as a β-lactamase-dependent prodrug
Ruddle, Carol C.,Smyth, Timothy P.
, p. 160 - 168 (2008/03/28)
The penam nucleus can be modified to behave as a β-lactamase-dependent 'prodrug' by incorporation of a vinyl ester side chain at the 6-position. Enzyme-catalysed hydrolysis of the β-lactam ring uncovers the thiazolidine-ring nitrogen as a nucleophile that
Penicillins as β-lactamase-dependent prodrugs: Enabling role of a vinyl ester exocyclic to the lactam ring
Ruddle, Carol C.,Smyth, Timothy P.
, p. 2332 - 2333 (2007/10/03)
Incorporation of a vinyl ester exocyclic to the β-lactam ring of a penicillin nucleus enables this to act as a β-lactamase-dependent prodrug - rapid release of the (unactivated) alkoxy component of the vinyl ester is triggered by enzyme-catalysed hydrolys
