Journal Article10.1360/ssc-2022-0217
Recent progress in hydroxynitrile lyases: utilization in the synthetic chemistry
TL;DR: In this article , the basic traits and principles of biocatalytic asymmetric hydrocyanation and nitroaldol reactions are summarized, as well as representative examples of recent bioactive asymmetric synthesis of bioactive compounds.
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Abstract: <p indent="0mm">As one of the few biocatalysts which can catalyze asymmetric C–C bond formation, hydroxynitrile lyases have emerged as attractive biocatalysts in terms of their high chemo- and enantioselectivity for the synthesis cyanohydrins and β-nitro alcohols under mild conditions. With the enabling technology on molecular biology and protein engineering, the application of hydroxynitrile lyases in asymmetric synthesis has been greatly expanded. We herein summarized the basic traits and principles of biocatalytic asymmetric hydrocyanation and nitroaldol reactions. In addition, the representative examples of recent biocatalytic asymmetric synthesis of bioactive compounds <italic>via</italic> hydrocyanation or nitroaldol reaction as key steps are exemplified, and the future directions are briefly discussed.
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References
Chemically Catalyzed Asymmetric Cyanohydrin Syntheses
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A Biocatalytic Henry Reaction—The Hydroxynitrile Lyase from Hevea brasiliensis Also Catalyzes Nitroaldol Reactions
Thomas Purkarthofer,Karl Gruber,Mandana Gruber-Khadjawi,Kerstin Waich,Wolfgang Skranc,Daniel Mink,Herfried Griengl +6 more
TL;DR: This work examined the addition of nitromethane to aldehydes in the presence of the hydroxynitrile lyase from Hevea brasiliensis and considered replacing HCN by other nucleophiles to be added to carbonyl compounds catalyzed by these enzymes.
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Synthesis and Reactions of Optically Active Cyanohydrins
TL;DR: A review of chiral cyanohydrins can be found in this article, where the authors discuss enantioselective addition of hydrogen cyanide (HCN), catalysed by the enzymes (R)-and (S)-oxynitrilase, to aldehydes and Ketones yielding (R) and (S) cyanohydrin, respectivity.
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Enzyme catalyzed cyanohydrin synthesis in organic solvents
TL;DR: In this article, the ESR spectrum for the diene 3 subjected to the same treatment is observed, and it is shown that the appearance voltage in the electrolysis is substantially lower than for 1.
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