Penicillin solid phase synthesis

Keywords Azitidinone Penicillin Solid phase synthesis (5-Lactam (5-Sultam Contents... 

Mata et al. also described a new and robust protocol for the solid-phase synthesis of 2(3-methyl substituted penam derivatives using Merrifield resin as support [210]. The work begins with immobilization of 6,6-dibromopenicillanic acid (171) onto Merrifield resin followed by oxidation with m-chloroperbenzoic acid (MCPBA) to obtain the resin-bound sulfoxide (173). The key-step involves the thermal rearrangement of the corresponding penicillin sulfoxide (Scheme 49). 

Scheme 50 Solid phase synthesis of penicillin using Merrifield resin and Wang resin...

Solid-phase techniques for the synthesis of bicylic (3-lactams have also been reviewed by Mata. Mata has also reported strategies for the solid-phase synthesis (and functionalization) of such compounds, with the aim of accessing libraries of antibiotics as well as enzyme inhibitors. For example, the feasibility of attaching penicillin antibiotics to Wang or Merrifield resin was investigated. 

DKPs are simple and easy to obtain and are quite common by-products of synthetic, spontaneous, and biological formation pathways. DKP formation has been well documented as side reactions of solid-phase and solution-phase peptide synthesis. In addition, DKPs have been shown to be decomposition products of various peptides, proteins, and other commercial pharmaceuticals. Cyclic dipeptides were found to be present in solutions of human growth hormone, bradykinin, histerlin, and solutions of agents within the classes of penicillins and cephalosporins. " DKPs are also enzymatically synthesized in several protists and in members of the plant kingdom. Hydrolysates of proteins and polypeptides often contain these compounds and they are commonly isolated from yeasts, lichens, and fungi. ... 

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