Chemo- and Stereoselective Cytochrome P450-BM3 Catalyzed Sulfoxidation of 
1-Thiochroman-4-ones

Wang, Jianbo; Ilie, Adriana; Reetz, Manfred T.

doi:10.1002/adsc.201700414

アイテム詳細

登録内容を編集ファイル形式で保存

一時保存へ追加

このアイテムの新しいバージョンが利用可能です:
https://pure.mpg.de/pubman/item/item_2451508_5

詳細要約

公開

学術論文

Chemo- and Stereoselective Cytochrome P450-BM3 Catalyzed Sulfoxidation of 1-Thiochroman-4-ones

MPS-Authors

Wang, Jianbo
Philipps-Universität Marburg, Fachbereich Chemie;
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons137019

Ilie, Adriana
Philipps-Universität Marburg, Fachbereich Chemie;
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58919

Reetz, Manfred T.
Philipps-Universität Marburg, Fachbereich Chemie;
Research Department Reetz, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Resource

There are no locators available

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

フルテキスト (公開)

公開されているフルテキストはありません

付随資料 (公開)

There is no public supplementary material available

引用

Wang, J., Ilie, A., & Reetz, M. T. (2017). Chemo- and Stereoselective Cytochrome P450-BM3 Catalyzed Sulfoxidation of 1-Thiochroman-4-ones. Advanced Synthesis & Catalysis. doi:10.1002/adsc.201700414.

引用: https://hdl.handle.net/11858/00-001M-0000-002D-71B7-2

要旨

Directed evolution utilizing an unconven- tional approach to saturation mutagenesis has been applied to cytochrome P450-BM3 as a catalyst in the asymmetric sulfoxidation of 1-thiochroman-4- one and two deriva tives thereof with complete che- moselectivity as well as ( S)- and (R)-selectivity on an optional ba sis. Whereas wild-type P450-BM3 shows in the case of the parent compound poor enantioselectivity in slight favor of the (S)-sulfoxide (er = 75:25), (S)-selectivity was enhanced to er = 93:7, while reversal of enantioselectivity favoring the (R )-sulfoxide was also achieved (er = 7:93). Two derivatives of the parent substrate underwent simi- lar stereoselective sulfoxidation reactions. Sulfox- ides of this type are of poten tial pharmaceutical in- terest. This biocatalytic approach nicely comple- ments synthetic methods.