« Previous AbstractThrombosed growing giant aneurysms of the vertebral artery: growth mechanism and management    Next AbstractThe presence of Drosophila melanogaster sex peptide-like immunoreactivity in the accessory glands of male Helicoverpa armigera »

Bioorg Med Chem

Title:		Synthesis of enantiomerically enriched drug precursors and an insect pheromone via reduction of ketones using commercially available carbonyl reductase screening kit 'Chiralscreen(R) OH'
Author(s):		Nagai T; Sakurai S; Natori N; Hataoka M; Kinoshita T; Inoue H; Hanaya K; Shoji M; Sugai T;
Address:		"Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan. Ichikawa Senior High School, 2-38-1, Motokitakata, Ichikawa 272-0816, Japan. Keio Shonan Fujisawa Junior & Senior High School, 5466, Endo, Fujisawa 252-0816, Japan. Department of Chemistry, School of Medicine, Keio University, 4-1-1, Hiyoshi, Kohoku-ku, Yokohama 223-8521, Japan. Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan. Electronic address: sugai-tk@pha.keio.ac.jp"
Journal Title:		Bioorg Med Chem
Year:		2018
Volume:		20170401
Issue:		7
Page Number:		1304 - 1313
DOI:		10.1016/j.bmc.2017.03.067
ISSN/ISBN:		1464-3391 (Electronic) 0968-0896 (Linking)
Abstract:		"Commercially available 'Chiralscreen(R) OH' starter kit containing five types of carbonyl reductases (E001, E007, E031, E039, and E078) was used for the reduction of several aromatic and aliphatic ketones to obtain enantiomerically enriched drug precursors and an insect pheromone. Almost stereochemically pure secondary alcohols, used in the synthesis of drugs such as (R)-rasagiline mesylate, (S)-rivastigmine, (R)-chlorphenesin carbamate, and (R)-mexiletine, and the insect pheromone (4S,5R)-sitophilure, were conveniently obtained. The enzymes worked well with ketones containing at least one non-bulky substituent at the carbonyl group. The diverse stereochemical preference of the above five carbonyl reductases was clarified"
Keywords:		Alcohol Oxidoreductases/chemistry/*metabolism Ketones/chemistry/*metabolism Molecular Structure Oxidation-Reduction Pheromones/*biosynthesis/chemistry Stereoisomerism Asymmetric reduction Carbonyl reductase Enzyme library 'Chiralscreen(R) OH';
Notes:		"MedlineNagai, Toshiya Sakurai, Saki Natori, Naoki Hataoka, Manaka Kinoshita, Takako Inoue, Hiroyoshi Hanaya, Kengo Shoji, Mitsuru Sugai, Takeshi eng Research Support, Non-U.S. Gov't England 2017/05/17 Bioorg Med Chem. 2018 Apr 1; 26(7):1304-1313. doi: 10.1016/j.bmc.2017.03.067. Epub 2017 Apr 1"