Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl) imidazolium- and triazolium-based ionic liquids

Paweł Borowiecki , Małgorzata Milner-Krawczyk , Jan Plenkiewicz

Abstract

Racemic 1-(β-hydroxypropyl)azoles were prepared by solvent-free direct regioselective ring opening of 1,2-propylene oxide with imidazole or 1,2,4-triazole. Lipase-catalyzed transesterification of alcohols with vinyl acetate resulted in kinetic enantiomers resolution. Separated (S)-enantiomers of (+)-1-(1H-imidazol-1-yl)propan-2-ol and (+)-1-(1H-1,2,4-triazol-1-yl)propan-2-ol were quaternized with alkyl bromides or iodides, yielding novel optically active ionic liquids. Racemic salts were tested against a wide range of microorganisms.
Author Paweł Borowiecki (FC / IBC / DDTB)
Paweł Borowiecki,,
- Department Of Drug Technology And Biotechnology
, Małgorzata Milner-Krawczyk (FC / IBC / DDTB)
Małgorzata Milner-Krawczyk,,
- Department Of Drug Technology And Biotechnology
, Jan Plenkiewicz (FC / IBC / DDTB)
Jan Plenkiewicz,,
- Department Of Drug Technology And Biotechnology
Journal seriesBeilstein Journal of Organic Chemistry, ISSN 1860-5397
Issue year2013
Vol9
Pages516-525
Publication size in sheets0.5
Keywords in Englishantibiotics, antifungal agents, double derivatization, enzyme catalysis, ionic liquids
ASJC Classification1605 Organic Chemistry
DOIDOI:10.3762/bjoc.9.56
URL http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-9-56
Languageen angielski
File
1860-5397-9-56.pdf 930.94 KB
Score (nominal)30
Score sourcejournalList
ScoreMinisterial score = 30.0, 02-02-2020, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 02-02-2020, ArticleFromJournal
Publication indicators Scopus Citations = 13; WoS Citations = 10; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 0.78; WoS Impact Factor: 2013 = 2.82 (2) - 2013=2.656 (5)
Citation count*4 (2015-03-03)
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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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