A method based on the use of whole lyophilized microbial cells has been developed for resolution of 2-alkanols. Firstly, the esterification of racemic 2-octanol with butyric acid was studied. Rhizopus oryzae CBS 112-07 grown on Tween 80 was selected as a suitable biocatalyst. Appropriate choice of solvent, temperature and reactant concentration allowed for highly selective esterification (>97% enantiomeric excess of R-ester, 41% molar conversion). Direct esterification of 2-octanol with butyric acid was compared with interesterification using different acylating reagents. The best results were obtained with butyric acid and tributyrin. Esterification of other racemic 2-alkanols (2-butanol, 2-pentanol, 2-hexanol, 2-heptanol) showed that chain length played a crucial role in enantioselectivity, since lower enatiomeric excesses were observed using short chain alcohols. A method based on the use of whole lyophilized microbial cells has been developed for resolution of 2-alkanols. Firstly, the esterification of racemic 2-octanol with burytic acid was studied. Rhizopus oryzae CBS 112-07 grown on Tween 80 was selected as a suitable biocatalyst. Appropriate choice of solvent, temperature and reactant concentration allowed for highly selective esterification (>97% enantiomeric excess of R-ester, 41% molar conversion). Direct esterification of 2-octanol with butyric acid was compared with interesterification using different acylating reagents. The best results were obtained with butyric acid and tributyrin. Esterification of other racemic 2-alkanols (2-butanol, 2-pentanol, 2-hexanol, 2-heptanol) showed that chain length played a crucial role in enantioselectivity, since lower enatiomeric excesses were observed using short chain alcohols.
Resolution of 2-alkanols by microbially-catalyzed esterification / F. Molinari, L. Mantegazza, R. Villa, F. Aragozzini. - In: JOURNAL OF FERMENTATION AND BIOENGINEERING. - ISSN 0922-338X. - 86:1(1998), pp. 62-64.
Resolution of 2-alkanols by microbially-catalyzed esterification
F. MolinariPrimo
;R. VillaPenultimo
;
1998
Abstract
A method based on the use of whole lyophilized microbial cells has been developed for resolution of 2-alkanols. Firstly, the esterification of racemic 2-octanol with butyric acid was studied. Rhizopus oryzae CBS 112-07 grown on Tween 80 was selected as a suitable biocatalyst. Appropriate choice of solvent, temperature and reactant concentration allowed for highly selective esterification (>97% enantiomeric excess of R-ester, 41% molar conversion). Direct esterification of 2-octanol with butyric acid was compared with interesterification using different acylating reagents. The best results were obtained with butyric acid and tributyrin. Esterification of other racemic 2-alkanols (2-butanol, 2-pentanol, 2-hexanol, 2-heptanol) showed that chain length played a crucial role in enantioselectivity, since lower enatiomeric excesses were observed using short chain alcohols. A method based on the use of whole lyophilized microbial cells has been developed for resolution of 2-alkanols. Firstly, the esterification of racemic 2-octanol with burytic acid was studied. Rhizopus oryzae CBS 112-07 grown on Tween 80 was selected as a suitable biocatalyst. Appropriate choice of solvent, temperature and reactant concentration allowed for highly selective esterification (>97% enantiomeric excess of R-ester, 41% molar conversion). Direct esterification of 2-octanol with butyric acid was compared with interesterification using different acylating reagents. The best results were obtained with butyric acid and tributyrin. Esterification of other racemic 2-alkanols (2-butanol, 2-pentanol, 2-hexanol, 2-heptanol) showed that chain length played a crucial role in enantioselectivity, since lower enatiomeric excesses were observed using short chain alcohols.Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.