Direct biosynthesis of poly(3-hydroxyalkanoates) bearing epoxide groups

The biosynthesis of poly(3-hydroxyalkanoates) (PHAs) by Pseudomonas cichorii YN2 cultured with C6-C12 1-alkenes was studied. PHAs containing repeating units with terminal epoxide groups were obtained when C7-C12 1-alkenes were fed separately as the only carbon source, but no epoxidized unit was detected when 1-hexene was fed. The content of epoxidized units in the polymers was in the range of 4-20 mol%, which was not dependent on the C atom length of the 1-alkene used as a substrate. The polymers produced undergo a glass transition at around -40 degrees C, and number average molecular weights were in the range of 150000-200000 as determined by GPC relative to polystyrene, with M(w)/M(n) ratios of 1.9-2.5. As an intermediate, the corresponding 1,2-epoxyalkane was found in the culture medium. According to this result, the epoxidation of the 1-alkene is the initial step in the synthetic pathway of the epoxy unit in the polymer.