Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the reaction rate of various nitrile...

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Published in:Journal of organic chemistry 1997-12, Vol.62 (26), p.9165-9172
Main Authors: Itoh, Toshiyuki, Mitsukura, Koichi, Kanphai, Wipa, Takagi, Yumiko, Kihara, Hiroshi, Tsukube, Hiroshi
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cited_by cdi_FETCH-LOGICAL-a361t-e804c0c5ce0a886e06bc3d1b47936c25ecd419427d59096a5833145e026a48f13
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container_end_page 9172
container_issue 26
container_start_page 9165
container_title Journal of organic chemistry
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creator Itoh, Toshiyuki
Mitsukura, Koichi
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description Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomehtyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.
doi_str_mv 10.1021/jo971288m
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title Thiacrown Ether Technology in Lipase-Catalyzed Reaction:  Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis
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