Chemoenzymatic synthesis of <i>N</i>-phenyl glycine derivatives via integration of Au/TiO<sub>2</sub> and enzyme as catalysts in water

Herein, we have developed a chemoenzymatic approach for the synthesis of <i>N</i>-phenyl glycine derivatives involving gold-catalyzed reduction of nitrophenol and engineered myoglobin-catalyzed chemoselective carbene insertion into the N–H bond over the O–H bond with alkyl diazo acetates using water as a solvent. In addition, the generality and synthetic utility of this chemoenzymatic approach was demonstrated by setting up the scale-up reactions of differently substituted nitroarenes and diazo compounds which in turn provides the N-phenyl glycine derivatives up to 85% isolated yields.

Publication Details

Journal
Figshare
Published
2025-01-01
DOI
https://doi.org/10.6084/m9.figshare.28478416
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
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Chemoenzymatic synthesis of N-phenyl glycine derivatives via integration of Au/TiO2 and enzyme as catalysts in water

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Cyclopropane Reaction Mechanisms
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Chemoenzymatic synthesis of N-phenyl glycine derivatives via integration of Au/TiO2 and enzyme as catalysts in water

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Abstract

Herein, we have developed a chemoenzymatic approach for the synthesis of <i>N</i>-phenyl glycine derivatives involving gold-catalyzed reduction of nitrophenol and engineered myoglobin-catalyzed chemoselective carbene insertion into the N–H bond over the O–H bond with alkyl diazo acetates using water as a solvent. In addition, the generality and synthetic utility of this chemoenzymatic approach was demonstrated by setting up the scale-up reactions of differently substituted nitroarenes and diazo compounds which in turn provides the N-phenyl glycine derivatives up to 85% isolated yields.

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Cyclopropane Reaction Mechanisms
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Chemoenzymatic synthesis of <i>N</i>-phenyl glycine derivatives via integration of Au/TiO<sub>2</sub> and enzyme as catalysts in water · Figshare (2025) | TGRS Research Map | TGRS