Synfacts 2009(1): 0106-0106  
DOI: 10.1055/s-0028-1087256
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Activation of Lipase by Chiral Imidazolium Cetyl-PEG10-Sulfate

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Hidetoshi Ohta
Y. Abe, T. Hirakawa, S. Nakajima, N. Okano, S. Hayase, M. Kawatsura, Y. Hirose, T. Itoh*
Tottori University and Amano Enzyme Ltd., Gifu, Japan
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
18. Dezember 2008 (online)

Significance

The chiral pyrrolidine-substituted imidazolium cetyl-PEG10-sulfate (d-ProMe, 3a) was prepared as an activating agent of Burkholderia cepacia lipase (lipase PS). Thus, the ion exchange reaction of chiral pyrrolidine-substituted imidazolium bromides 1a,b with 2 (1.0 equiv) gave the corresponding imidazolium cetyl-PEG10-sulfate 3a,b (eq. 1). Coating treatment of lipase PS with 3a by the lyophilization process afforded the coated enzyme d-ProMe-PS (eq. 2). Transesterification of ()-1-phenylethanol (4) with vinyl acetate (1.5 equiv) was carried out in the presence of d-ProMe-PS to afford a mixture of (R)-5 (37% yield, >99% ee) and unreacted (S)-4 (39% yield, 97% ee) (eq. 3).