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April 26, 2026ACS Catalysis0 citations

Constructing a Biosynthetic Pathway of α-Arylglycines via C1 Extension of Aldehydes

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YLYu LiMSMengqian SongJFJinhui Feng

Key Points

  • This research aims to develop an efficient biosynthetic pathway for the asymmetric synthesis of α-arylglycines from C1 molecules.
  • Engineered a multienzyme biosynthetic pathway for the conversion of formaldehyde and aromatic aldehydes into α-arylglycines.
  • Used ThDP-dependent hydroxymethylation, GOase-catalyzed oxidation, and amino acid dehydrogenase-catalyzed reductive amination.
  • Developed one-pot cascade reactions to achieve high isolated yields of α-arylglycines.
  • Achieved 80% isolated yield of 2-oxo-2-phenylacetic acid with a space-time yield of 6.0 g·L−1·h−1.
  • One-pot, two-step cascade resulted in α-arylglycines with 56−99% enantiomeric excess and 63−98% yields.
  • Extended strategy yielded enantio-complementary α-arylglycines in isolated yields of 62−90%.

Abstract

The use of C1 molecules as feedstocks for producing high-value chemicals is an attractive yet technically inefficient process. Optically pure α-arylglycines are valuable pharmaceutical intermediates, but their efficient asymmetric biosynthesis from C1 molecules has not been reported. Herein, a multienzyme biosynthetic pathway was successfully designed and implemented for the asymmetric synthesis of α-arylglycines from the C1 molecule formaldehyde (HCHO) and aromatic aldehydes, which involved thiamine diphosphate (ThDP)-dependent enzyme-catalyzed hydroxymethylation, galactose oxidase (GOase)-catalyzed oxidation, and d or l-amino acid dehydrogenase-catalyzed reductive amination. The engineered GOase M3-5 mutant (Y329I/M330F/S331R) demonstrated enhanced catalytic efficiency, achieving 2-oxo-2-phenylacetic acid (1c) in an 80% isolated yield with a space-time yield of 6.0 g·L−1·h−1. A one-pot, two-step cascade reaction combining oxidation and reductive amination was then developed to afford α-arylglycines and leucine with 56−99% ee and 63−98% isolated yields. Furthermore, this strategy was extended to a one-pot, three-step cascade, enabling the synthesis of enantio-complementary α-arylglycines from HCHO, aromatic aldehydes, and ammonium chloride in high isolated yields (62−90%). This study provides a practical and efficient strategy for producing high-value chiral amino acids from simple aldehydes.

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Cite This Study

Li et al. (2026) studied this question.

synapsesocial.com/papers/69edad274a46254e215b4c8bhttps://doi.org/10.1021/acscatal.6c00647
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