Lipase made active in hydrophobic media by coupling with polyethylene glycol |
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Authors: | Y Kodera H Nishimura A Matsushima M Hiroto Y Inada |
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Affiliation: | (1) Human Science and Technology Center, Department of Materials Science and Technology, Toin University of Yokohama, 1614 Kurogane-cho, Midori-ku, 225 Yokohama, Japan |
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Abstract: | Lipases from various microorganisms were chemically modified with polyethylene glycol derivatives: 2,4-bisO-methoxypoly(ethylene glycol)]-6-chloro-s-triazine (activated PEG2, a chain-shaped polymer) and copolymer of polyoxyethylene allyl methyl diether and maleic anhydride (activated PM, a comb-shaped
polymer). Because each polymer is amphipathic, the modified lipases become soluble not only in aqueous solution but also in
hydrophobic media. They exhibit potent catalytic actions for ester synthesis and ester exchange reactions, the reverse reaction
of hydrolysis, in transparent organic solvents and also in oily substrates without organic solvents. With PEG2-lipases, macrocyclic lactone and gefarnate (geranyl farnesylacetate) were synthesized in high yields from 16-hydroxy-hexadecanoic
acid ethyl ester and from farnesylacetic acid and geraniol in organic solvents, respectively. The modified lipase catalyzed
the esterification preferentially with the (R)-isomer of secondary alcohols. Because the ester synthesis reactions with modified lipase proceeded in the transparent benzene
system, the kinetic parameters (Michaelis constant and maximum velocity) were obtained by reciprocal plotting according to
the Michaelis equation. With comb-shaped polymer as modifier, PM-lipase catalyzed effectively the reverse reaction of hydrolysis
in organic solvents. The properties of each modified lipase are discussed in relation to those of the nonmodified lipase.
Presented at the 84th Annual Meeting of the American Oil Chemists' Society held on April 25–29, 1993, in Anaheim, CA. |
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Keywords: | Activated PEG2 activated PM esterification heatstability lactonization lipase optical resolution organic solvents polyethylene glycol |
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