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

Abstract

A 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.
Author Paweł Borowiecki (FC / IBC / DDTB)
Paweł Borowiecki,,
- Department Of Drug Technology And Biotechnology
, Marcin Fabisiak (FC / IBC / DDTB)
Marcin Fabisiak,,
- Department Of Drug Technology And Biotechnology
, Zbigniew Ochal (FC / IBC / DDTB)
Zbigniew Ochal,,
- Department Of Drug Technology And Biotechnology
Journal seriesTetrahedron, ISSN 0040-4020
Issue year2013
Vol69
No23
Pages4597-4602
Publication size in sheets0.5
Keywords in English1,3-Benzothiazoles, lipase-catalyzed kinetic resolution, double derivatization, fungicidal activity
ASJC Classification1605 Organic Chemistry; 3002 Drug Discovery; 1303 Biochemistry
DOIDOI:10.1016/j.tet.2013.04.014
URL http://www.sciencedirect.com/science/article/pii/S0040402013005401
Languageen angielski
File
tetrahedron_2013_69_4597.pdf 335.15 KB
Score (nominal)30
Score sourcejournalList
ScoreMinisterial score = 30.0, 25-02-2020, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 25-02-2020, ArticleFromJournal
Publication indicators Scopus Citations = 13; WoS Citations = 13; GS Citations = 1.0; Scopus SNIP (Source Normalised Impact per Paper): 2014 = 0.905; WoS Impact Factor: 2013 = 2.817 (2) - 2013=2.772 (5)
Citation count*1 (2014-04-14)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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