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Enantioselecive Sulfoxidations Catalyzed by Horseradish Peroxidase, Manganese Peroxidase,and Myeloperoxidase

机译:辣根过氧化物酶,锰过氧化物酶和髓过氧化物酶催化的对映体硫氧化

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摘要

Horseradish peroxidase (HRP),myeloperoxidase (MPO),and manganese peroxidase (MnP) have been shown to catalyze the asymmetric sulfoxidation of thioanisole. When H_2O_2 was added stepwise to MPO, amaximal yield of 78% was obtained at pH 5 (ee 23%), whereas an optimum in the enantiomeric excess (32%, (R)-sulfoxide) was found at pH 6 (60% yield). For MnP a yield of 18% and a high enantiomeric excess of 91% of the (S)-sulfoxide were obtained at pH 5 and a yield of 36% and an ee of 87% at pH 7.0. Optimization of the conversion catalyzed by horseradish peroxidase at pH 7.0 by controlled continuous addition of hydrogen peroxide during turnover and monitoring the presence of native enzyme as well as of intermediates I,II,and III led to the formaiton of the sulfoxide in high yield (100%)and moderate enantioselectivity (60%, (S)-surfoxide).
机译:辣根过氧化物酶(HRP),髓过氧化物酶(MPO)和锰过氧化物酶(MnP)已被证明可催化硫代茴香醚的不对称硫氧化。当将H_2O_2逐步添加到MPO中时,在pH 5时最大产率为78%(ee 23%),而在pH 6时对映体过量最佳(32%,(R)-亚砜)(产率60%) )。对于MnP,在pH 5时获得了18%的产率和(S)亚砜的91%的高对映体过量,在pH 7.0时获得了36%的产率和87%的ee。通过在周转期间控制连续添加过氧化氢并监测天然酶以及中间体I,II和III的存在,优化了在pH 7.0下辣根过氧化物酶催化的转化率的优化,从而导致了亚砜的高产(100 %)和中等对映选择性(60%,(S)-过氧化物)。

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