Co-solvent enhancement of enantioselectivity in lipase-catalysed hydrolysis of racemic esters. A process for production of homochiral C-3 building blocks using lipase B from Candida antarctica
✍ Scribed by Trond Vidar Hansen; Viggo Waagen; Vassilia Partali; Henrik W Anthonsen; Thorleif Anthonsen
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- English
- Weight
- 306 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0957-4166
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✦ Synopsis
Lipase-catalysed hydrolysis of butanoates of 3-methoxy-1-(phenylmethoxy)-2-propanol and 3-chloro-l-(phenylmethoxy)-2-propanol with various lipases gave low enantioselectivity, E. By additon of water miscible organic cosolvents, in particular tert-butanol and acetone, the E-value was raised from 7 to 220 for the useful chloro derivative. This finding has led to proposal of a process for production of homochiral C-3 synthons such as both enantiomers of phenylmethyl glycidyl ether starting from racemic epichlorohydrin. NMR studies of lipase B from Candida antarctica show that the conformation most likely is not changed upon addition of up to 50% acetone. Nuclear Overhauser effects were observed upon irradiation of the phenyl protons of the substrate only in the presence of enzyme thus indicating an interaction between the two.