Synfacts 2008(2): 0210-0210  
DOI: 10.1055/s-2007-992518
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Easy Separation of Optically Active Products

Contributor(s): Uozumi Yasuhiro, Yoichi M. A. Yamada, Toshihiro Watanabe
M. Okudomi, M. Shimojo, M. Nogawa, A. Hamanaka, N. Taketa, K. Matsumoto*
Meisei University, Tokyo, Japan
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Publikationsverlauf

Publikationsdatum:
23. Januar 2008 (online)

Significance

The kinetic resolution by enzymatic hydrolysis of PEG-supported carbonates was reported. Thus, a water-soluble substrate 1 was prepared via immobilization of ()-1-phenylethanol onto a monomethoxy PEG5000 (MPEG5000; average Mw 5,000) through a phenylethyl carbonate linker. Enantioselective hydrolysis of 1 with PPL (porcine pancreas lipase) was performed in hexane/0.1 M phosphate buffer (pH 6.5) to give (R)-2 in 24% conversion with 99% ee (E value = 270). The hydrolysis of 5 under similar conditions afforded (R)-6 in 3% yield with 91% ee (E value = 23) and MPEG-supported 5.