Selective oxidation of penicillin G with hydrogen peroxide and with enzymatically generated peroxyoctanoic acid

Abstract

Two convenient procedures for the oxidation of penicillin G into penicillin G 1‐(s)‐oxide have been developed. Both the mild oxidation with enzymatically generated peroxyoctanoic acid and the attractive and simple oxidation with the sole use of hydrogen peroxide are valuable alternatives for the commercial oxidation with 40% peroxyacetic acid.

The rational design of semisynthetic peroxidases

“…Comparable ee values and reaction rates were observed in carboxylate buffers (acetate and formate) and non-carboxylate buffers (MES, HEPES, and Tris). This demonstrates that a carboxylate group is not essential for catalysis and ruled out the in situ formation of percarboxylic acids as observed with lipases (Björkling et al, 1992;De Zoete et al, 1993) and metal-free bacterial haloperoxidases (Picard et al, 1997). In contrast, phosphate and citrate completely inhibited the enantioselective oxidation.…”

Enantioselective sulfoxidation mediated by vanadium-incorporated phytase: a hydrolase acting as a peroxidase

“…Ammonium chloride and MES ‡ were also effective, giving conversions and (ee values) after 5 h of 74% (35%) and 71% (43%), respectively, in experiments performed at 4 mM H 2 O 2 . This rules out the in situ formation of peroxycarboxylic acids (from the carboxylate buffers) as observed with lipases 11 and metal-free bacterial haloperoxidases. 12 The optimum pH was 5.1 which coincides with that of the natural reaction of phytase.…”

Predicting Autoxidation of Sulfides in Drug-like Molecules Using Quantum Mechanical/Density Functional Theory Methods

“…The compounds studied include 23 commercial drugs, 35 drug-like compounds, and 26 small organic compounds, which covers 50 different sulfide moieties and a wide range of chemical space. Part of the data set is built from reported degradation studies. − Synthetic oxidation reactions are obtained from the Reaxys database . Thirty-three compounds in the data set contain more than one sulfide.…”