Use of lipases in the resolution of racemic ibuprofen

Annikka Mustranta

Research output: Contribution to journalArticleScientificpeer-review

158 Citations (Scopus)

Abstract

Resolution of (R,S)-ibuprofen enantiomers by esterification in different organic solvents was studied using Candida cylindracea lipase.
This enzyme preparation had high enantiospecificity for S(+)-ibuprofen in the esterification reaction of a racemic ibuprofen with primary alcohols. The esterification yields of secondary alcohols were much lower than those of primary alcohols.
Esterification with tertiary alcohols was not observed. The synthesis of esters was profoundly affected by the amount of water in the reaction mixture. C. cylindracea lipase was active only in very hydrophobic solvents.
The esterification activity of the lipase was reduced significantly by addition of water. The R- and S-enantiomers of ibuprofen were determined without derivatization by HPLC using a chiral column.
Original languageEnglish
Pages (from-to)61-66
JournalApplied Microbiology and Biotechnology
Volume38
Issue number1
DOIs
Publication statusPublished - 1992
MoE publication typeA1 Journal article-refereed

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