Nocardia corallina epoxidation

This is not the case for a Rhodococcus rhodochrous strain that affords 1,2-epoxyalkanes from short-chain terminal olefins. Indeed, in the latter case, no product inhibition has been observed [106]. However, the ee s obtained were not determined, and it seems probable that they were quite low. On the other hand, a Nocardia corallina strain was described that afforded the corresponding 1,2-(i )-epoxy-2-methylalkane with ee s as high as 90% depending on the chain length [ 107]. These epoxides were used as chiral building blocks to prepare prostaglandin co-chains. 

Chiral epoxide Alkene monooxygenase Nocardia corallina... 

Scheme 2.156 Epoxidation of styrene derivatives and branched alkenes using cloned monooxygenase and Nocardia corallina...

Alkene monooxygenase (AMO) from Rhodococcus rhodochrous B-276 (also known as Nocardia corallina) is a multicomponent oxygenase that catalyzes the stereoselective insertion of an oxygen atom from O2 into aliphatic alkenes, yielding the corresponding chiral epoxides (Table 1) [151], This reaction is the first step in the pathway of the alkene metabolism. AMO utilizes substrates ranging from C3-... 

---