Engineering Baker's Yeast to Perform Enantioselective Oxidations and Applications to Organic Synthesis

本研究的重点是利用酵母菌株表达有机合成中常用的酶。要研究的特定氧化酶包括环己酮单加氧酶、黄素单加氧酶和细胞色素P-450‘S。这些酶不需要辅因子，将等同于手性间氯过氧苯甲酸，其形式将与去手性试剂本身一样易于使用。它们将适用于进行烯烃环氧化、硫醚氧化(到手性亚砜)和Baeyer-Villiger反应等转化。通过这一奖项，合成有机计划支持佛罗里达大学化学系的乔恩·D·斯图尔特博士的研究。斯图尔特教授将把他的工作重点放在酵母表达的酶上，这些酶旨在进行有机合成中的对映选择性反应。除了形成光学活性产物，用于制备具有重要生物学特性的立体化学复杂体系外，这些酶都使用分子氧，而不是有机氧化剂，这使得它们从经济和环境角度来看都很有吸引力。

The focus of this research is the use of yeast strains to express enzymes of general utility in organic synthesis. The specific oxidative enzymes to be studied include cyclohexanone monooxygenase, flavin monooxygenase and cytochrome P-450's. These enzymes will not require cofactors and will be the equivalent of a chiral m-chloroperoxybenzoic acid in a form that will be as easy to use as the achiral reagent itself. They will be applicable to carry out such transformations as olefin epoxidations, thioether oxidations (to chiral sulfoxides) and Baeyer-Villiger reactions. With this award the Synthetic Organic Program is supporting the research of Dr. Jon D. Stewart of the Department of Chemistry of the University of Florida. Professor Stewart will focus his work on yeast-expressed enzymes designed to carry out enantioselective reactions in organic synthesis. Besides formation of optically active products which are useful for the preparation of stereochemically complex systems that have important biological properties, these enzymes all use molecular oxygen, rather than an organic oxidant, which makes them attractive from both an economic and environmental standpoint