@article{9df888d937cd40e5b864b4709248ee3b,
title = "Control of enantioselectivity in the enzymatic reduction of halogenated acetophenone analogs by substituent positions and sizes",
abstract = "We utilized acetophenone reductase from Geotrichum candidum NBRC 4597 (GcAPRD), wild type and Trp288Ala mutant, to reduce halogenated acetophenone analogs to their corresponding (S)- and (R)-alcohols beneficial as pharmaceutical intermediates. Reduction by wild type resulted in excellent (S)-enantioselectivity for all of the substrates tested. Meanwhile, reduction by Trp288Ala resulted in high (R)-enantioselectivity for the reduction of 4′ substituted acetophenone and 2′-trifluoromethylacetophenone. In addition to that, we were able to control the enantioselectivity of Trp288Ala by the positions and sizes of the halogen substituents.",
keywords = "Alcohol dehydrogenase, Asymmetric reduction, Enantioselectivity control, Halogenated acetophenone analogs",
author = "Koesoema, {Afifa Ayu} and Standley, {Daron M.} and Shusuke Ohshima and Mayumi Tamura and Tomoko Matsuda",
note = "Funding Information: The authors acknowledged Professor Miki Senda and Professor Toshiya Senda from High Energy Accelerator Research Organization (KEK), Japan, for the help with the crystallization of enzymes and valuable discussions. This work was supported by the Japan Society for the Promotion of Science , Japan (grant number JP16K05864 ) to Tomoko Matsuda and the Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED , Japan (grant number 19am0101108j0003) to Daron M. Standley. Funding Information: The authors acknowledged Professor Miki Senda and Professor Toshiya Senda from High Energy Accelerator Research Organization (KEK), Japan, for the help with the crystallization of enzymes and valuable discussions. This work was supported by the Japan Society for the Promotion of Science, Japan (grant number JP16K05864) to Tomoko Matsuda and the Platform Project for Supporting Drug Discovery and Life Science Research (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from AMED, Japan (grant number 19am0101108j0003) to Daron M. Standley. Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",
year = "2020",
month = apr,
day = "30",
doi = "10.1016/j.tetlet.2020.151820",
language = "English",
volume = "61",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "18",
}