Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology & College of Pharmaceutical Engineering and Life Sciences, Changzhou University, Changzhou, 213164, China,
Appl Microbiol Biotechnol. 2013 Dec;97(24):10329-37. doi: 10.1007/s00253-013-5258-2. Epub 2013 Oct 5.
Enantiopure sulfoxides can be prepared via the asymmetric oxidation of sulfides using sulfide monooxygenases. The n-octane-water biphasic system was chosen for the bio-oxidation of a water-insoluble phenyl methyl sulfide (PMS) by Rhodococcus sp. CCZU10-1. In this n-octane-water system, the optimum reaction conditions were obtained. (S)-phenyl methyl sulfoxide ((S)-PMSO) with >99.9 % enantiomeric excess formed at 55.3 mM in the n-octane-water biphasic system. Using fed-batch method, a total of 118 mM (S)-PMSO accumulated in 1-L reaction mixture after the 7th feed, and no (R)-PMSO and sulfone were detected. Moreover, Rhodococcus sp. CCZU10-1 displayed fairly good activity and enantioselectivity toward other sulfides. In conclusion, Rhodococcus sp. CCZU10-1 is a promising biocatalyst for synthesizing highly optically active sulfoxides.
手性纯亚砜可以通过亚砜单加氧酶不对称氧化硫化物来制备。选择正辛烷-水两相体系来进行水中不溶的苯基甲基硫醚（PMS）的生物氧化，所用菌株为 Rhodococcus sp. CCZU10-1。在该正辛烷-水体系中，得到了最佳的反应条件。在正辛烷-水两相体系中，（S）-苯基甲基亚砜（（S）-PMSO）以大于 99.9%的对映过量形成，浓度为 55.3mM。采用分批补料法，在第 7 次补料后，在 1-L 反应混合物中总共积累了 118mM 的（S）-PMSO，未检测到（R）-PMSO 和砜。此外，Rhodococcus sp. CCZU10-1 对其他硫化物也表现出相当好的活性和对映选择性。总之，Rhodococcus sp. CCZU10-1 是一种很有前途的生物催化剂，可用于合成高光学活性的亚砜。
