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Cited by 564

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Improved Preparation and Use of Room-Temperature Ionic Liquids in Lipase-Catalyzed Enantio- and Regioselective Acylations

Park, Seongsoon, Kazlauskas, Romas J.·2001·The Journal of Organic Chemistry
DOI 10.1021/jo015761e
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Abstract

Polar organic solvents such as methanol or N-methylformamide inactivate lipases. Although ionic liquids such as 3-alkyl-1-methylimidazolium tetrafluoroborates have polarities similar to these polar organic solvents, they do not inactivate lipases. To get reliable lipase-catalyzed reactions in ionic liquids, we modified their preparation by adding a wash with aqueous sodium carbonate. Lipase-catalyzed reactions that previously did not occur in untreated ionic liquids now occur at rates comparable to those in nonpolar organic solvents such as toluene. Acetylation of 1-phenylethanol catalyzed by lipase from Pseudomonas cepacia (PCL) was as fast and as enantioselective in ionic liquids as in toluene. Ionic liquids permit reactions in a more polar solvent than previously possible. Acetylation of glucose catalyzed by lipase B from Candida antarctica (CAL-B) was more regioselective in ionic liquids because glucose is up to one hundred times more soluble in ionic liquids. Acetylation of insoluble glucose in organic solvents yielded the more soluble 6-O-acetyl glucose, which underwent further acetylation to give 3,6-O-diacetyl glucose (2-3:1 mixture). However, acetylation of glucose in ionic liquids yielded only 6-O-acetyl glucose (>13:1 and up to >50:1).

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Authors
Park, S., & Kazlauskas, R. J.
Venue
The Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Published
2001-11-09
Volume
66
Issue
25
Pages
8395-8401
ISSN
  • 0022-3263 (ISSN-L)
  • 1520-6904
DOI
10.1021/jo015761e
OpenAlex
W2011287317
Cited by
564
References
0
FWCI
10.64
Type
journal article
Language
en
Open access
closed

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