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<p>Human carbonic anhydrase II (hCAII) is a reported biocatalyst for stereoselective reduction of aryl-alkyl-substituted ketones using phenylsilane as an abiotic hydride ion source. During studies investigating the substrate scope of hCAII/PhSiH<sub>3</sub>, we examined the reduction of 1-phenyl-1,2-propanedione under different conditions. In the presence of 2–6 equivalents of PhSiH<sub>3</sub>, we unexpectedly observed exclusive formation of enantiopure <i>anti</i>/<i>syn</i>-1-phenylpropane-1,2-diols (PPDs). The hCAII/PhSiH<sub>3</sub>-catalyzed reduction of racemic and enantiopure forms of 2-hydroxy-1-phenylpropan-1-one (HPP) and phenylacetylcarbinol (PAC) intermediates to give 1,2-diols is described. Experimental studies on 2-, 3-, and 4-substituted phenyl-1,2-propanediones and two heteroaromatic analogs revealed substituent effects on the regio- and stereoselectivity of the reduction, which were rationalized by computational studies on the unsubstituted and 4-substituted phenyl derivatives. The preparative utility of the optimized biocatalytic production of 1,2-diols is demonstrated. The combined results reveal how mechanistic knowledge of hCAII/PhSiH<sub>3</sub>-catalyzed reduction enabled the development of a scalable method for the synthesis of chiral 1,2-diols.</p>

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Human carbonic anhydrase II as a versatile biocatalyst for the synthesis of chiral aryl-1,2-diols

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  • 发表日期：

    2026年7月28日

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  • Laura Edit Barabás,
  • Diana Maria Scrob,
  • Monica Ioana Toşa,
  • Jürgen Brem,
  • László Poppe,
  • Christopher J. Schofield,
  • Csaba Paizs

摘要

Human carbonic anhydrase II (hCAII) is a reported biocatalyst for stereoselective reduction of aryl-alkyl-substituted ketones using phenylsilane as an abiotic hydride ion source. During studies investigating the substrate scope of hCAII/PhSiH3, we examined the reduction of 1-phenyl-1,2-propanedione under different conditions. In the presence of 2–6 equivalents of PhSiH3, we unexpectedly observed exclusive formation of enantiopure anti/syn-1-phenylpropane-1,2-diols (PPDs). The hCAII/PhSiH3-catalyzed reduction of racemic and enantiopure forms of 2-hydroxy-1-phenylpropan-1-one (HPP) and phenylacetylcarbinol (PAC) intermediates to give 1,2-diols is described. Experimental studies on 2-, 3-, and 4-substituted phenyl-1,2-propanediones and two heteroaromatic analogs revealed substituent effects on the regio- and stereoselectivity of the reduction, which were rationalized by computational studies on the unsubstituted and 4-substituted phenyl derivatives. The preparative utility of the optimized biocatalytic production of 1,2-diols is demonstrated. The combined results reveal how mechanistic knowledge of hCAII/PhSiH3-catalyzed reduction enabled the development of a scalable method for the synthesis of chiral 1,2-diols.