Easy separation of optically active products by enzymatic hydrolysis of soluble polymer-supported substrates

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Abstract

The easy separation of optically active compounds from enzymatic kinetic resolution products by simple precipitation using poly(ethylene glycol)(PEG)-supported carbonates is disclosed. The water-soluble substrate was prepared by the immobilization of (±)-1-phenylethanol onto a middle-molecular weight (av Mw5000) monomethoxy PEG (MPEG) through a carbonate linker. The enantioselective hydrolysis using Lipase from porcine pancreas (PPL; Type II, Sigma) in a mixed solvent (hexane/buffer = 9:1) proceeded to afford the corresponding optically active compounds. In this system, the separation of the products was achieved by a simple procedure without laborious column chromatography. A hydrophobic spacer between the MPEG moiety and the carbonate linker affected both the reactivity and enantioselectivity, and the substrate with a phenylethyl spacer was hydrolyzed with the highest enantioselectivity (E value = 270). © 2007 Elsevier Ltd. All rights reserved.

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Okudomi, M., Shimojo, M., Nogawa, M., Hamanaka, A., Taketa, N., & Matsumoto, K. (2007). Easy separation of optically active products by enzymatic hydrolysis of soluble polymer-supported substrates. Tetrahedron Letters, 48(48), 8540–8543. https://doi.org/10.1016/j.tetlet.2007.09.141

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