Modular assembly of chiral amino acid derivatives and peptides from commonly available feedstocks

α-Amino acids are fundamental components of proteins and natural molecules, with non-natural variants highly valued in both academia and industry for their ability to tune chemical, physical, and pharmaceutical properties. Herein, we report a photoredox-catalyzed protocol for the synthesis of optically active α-amino amides from readily available aldehydes, amines, and formamides. A dual catalytic system combining a chiral sodium phosphate with tetrabutylammonium decatungstate (TBADT) under visible light enables this transformation. The process achieves high enantioselectivity and allows two-step conversion to free amino acids without significant racemization. Consequently, diverse, synthetically useful structures-including β-branched and α,β-diamino acid derivatives, glycosylated amino acids, isotopically labeled compounds (deuterium and <sup>15</sup>N), and peptides-have been rapidly constructed. Flow chemistry further broadens substrate tolerance and eliminates prefunctionalization steps. Here, we show that leveraging TBADT-driven carbamoyl radical generation and chiral catalysis provides a practical route to diverse chiral scaffolds, thereby advancing peptide synthesis and drug discovery.

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Publication Details

Journal
Nature Communications
Published
2025-12-30
DOI
https://doi.org/10.1038/s41467-025-68073-w
Citations
1
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.94

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article

Modular assembly of chiral amino acid derivatives and peptides from commonly available feedstocks

Wan-Yu Wang, Zhi-Yong Han, Liu-Zhu Gong, Wei-Wei Ding et al.
1 citations
Nature Communications
Radical Photochemical Reactions
0.94
article

Modular assembly of chiral amino acid derivatives and peptides from commonly available feedstocks

Wan-Yu Wang, Zhi-Yong Han, Liu-Zhu Gong, Wei-Wei Ding, Zhi-Yuan He
article en
1 citations

Abstract

α-Amino acids are fundamental components of proteins and natural molecules, with non-natural variants highly valued in both academia and industry for their ability to tune chemical, physical, and pharmaceutical properties. Herein, we report a photoredox-catalyzed protocol for the synthesis of optically active α-amino amides from readily available aldehydes, amines, and formamides. A dual catalytic system combining a chiral sodium phosphate with tetrabutylammonium decatungstate (TBADT) under visible light enables this transformation. The process achieves high enantioselectivity and allows two-step conversion to free amino acids without significant racemization. Consequently, diverse, synthetically useful structures-including β-branched and α,β-diamino acid derivatives, glycosylated amino acids, isotopically labeled compounds (deuterium and <sup>15</sup>N), and peptides-have been rapidly constructed. Flow chemistry further broadens substrate tolerance and eliminates prefunctionalization steps. Here, we show that leveraging TBADT-driven carbamoyl radical generation and chiral catalysis provides a practical route to diverse chiral scaffolds, thereby advancing peptide synthesis and drug discovery.

Nature CommunicationsVol. 17(1)
University of Science and Technology of China (CN), Hefei National Center for Physical Sciences at Nanoscale (CN)
National Natural Science Foundation of China
Industry, innovation and infrastructure
Openalex Percentile: Top 19%
Radical Photochemical Reactions
0.94
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Modular assembly of chiral amino acid derivatives and peptides from commonly available feedstocks — Wan-Yu Wang, Zhi-Yong Han, et al. · Nature Communications (2025) | TGRS Research Map | TGRS