Lipase-catalyzed kinetic resolution of 1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol with antifungal activity: a comparative study of transesterification versus hydrolysis
Paweł Borowiecki , Marcin Fabisiak , Zbigniew Ochal
AbstractA study of chemoenzymatic synthesis of both enantiomers of 1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-ol was carried out. Several commercially available lipase preparations were tested as biocatalysts in the kinetic resolution process of target compound by enantioselective transesterification and/or hydrolysis. CAL-B (Novozym 435) was found to be the optimal catalyst. The lipase-mediated hydrolysis approach appeared to be superior to the transesterification reaction. Absolute configuration of the obtained alcohol was postulated, applying modified Mosher's methodology. The inhibitory activity of the synthesized benzothiazole derivatives against pathogenic fungi was checked.
|Journal series||Tetrahedron, ISSN 0040-4020|
|Publication size in sheets||0.5|
|Keywords in English||1,3-Benzothiazoles, lipase-catalyzed kinetic resolution, double derivatization, fungicidal activity|
|ASJC Classification||; ;|
|Score|| = 30.0, 25-02-2020, ArticleFromJournal|
= 30.0, 25-02-2020, ArticleFromJournal
|Publication indicators||= 13; = 13; = 1.0; : 2014 = 0.905; : 2013 = 2.817 (2) - 2013=2.772 (5)|
|Citation count*||1 (2014-04-14)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.