Tailored amination enables switchable synthesis of α- and γ-amino acid derivatives from extended quinone methides
Abstract Unnatural α- and γ-amino acids display a diverse range of biological activities and serve as crucial intermediates in pharmaceutical production. Specifically, the synthesis of such molecules has been highly sought after in both academia and industry. Nevertheless, their direct synthesis fro...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-07-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-60749-7 |
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| author | Chao-Gang Zhang Yu-Ping Tang Qingqin Huang Yong-Ke Qiu Hailong Yan Lei Dai |
| author_facet | Chao-Gang Zhang Yu-Ping Tang Qingqin Huang Yong-Ke Qiu Hailong Yan Lei Dai |
| author_sort | Chao-Gang Zhang |
| collection | DOAJ |
| description | Abstract Unnatural α- and γ-amino acids display a diverse range of biological activities and serve as crucial intermediates in pharmaceutical production. Specifically, the synthesis of such molecules has been highly sought after in both academia and industry. Nevertheless, their direct synthesis from simple bulk feedstocks has remained largely unexplored, and the switchable synthesis of α- and γ-amino acids through a shared intermediate has never been documented. We disclose herein a four-component reaction involving readily available bulk chemicals to facilitate the switchable synthesis of α- and γ-amino acids from a shared extended p-quinone methide through a tailored amination strategy. A diverse array of amines, including several unmodified drug molecules, along with various other nucleophiles, are readily utilized as suitable substrates in this reaction. We believe this work could inspire future intensive efforts toward the switchable synthesis of amino acids in a practical and efficient manner. |
| format | Article |
| id | doaj-art-419fef7cc2ac4ea896183d3d43a89d0a |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-419fef7cc2ac4ea896183d3d43a89d0a2025-08-20T03:45:35ZengNature PortfolioNature Communications2041-17232025-07-0116111010.1038/s41467-025-60749-7Tailored amination enables switchable synthesis of α- and γ-amino acid derivatives from extended quinone methidesChao-Gang Zhang0Yu-Ping Tang1Qingqin Huang2Yong-Ke Qiu3Hailong Yan4Lei Dai5Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing UniversityChongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing UniversityChongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing UniversityChongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing UniversityChongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing UniversityChongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing UniversityAbstract Unnatural α- and γ-amino acids display a diverse range of biological activities and serve as crucial intermediates in pharmaceutical production. Specifically, the synthesis of such molecules has been highly sought after in both academia and industry. Nevertheless, their direct synthesis from simple bulk feedstocks has remained largely unexplored, and the switchable synthesis of α- and γ-amino acids through a shared intermediate has never been documented. We disclose herein a four-component reaction involving readily available bulk chemicals to facilitate the switchable synthesis of α- and γ-amino acids from a shared extended p-quinone methide through a tailored amination strategy. A diverse array of amines, including several unmodified drug molecules, along with various other nucleophiles, are readily utilized as suitable substrates in this reaction. We believe this work could inspire future intensive efforts toward the switchable synthesis of amino acids in a practical and efficient manner.https://doi.org/10.1038/s41467-025-60749-7 |
| spellingShingle | Chao-Gang Zhang Yu-Ping Tang Qingqin Huang Yong-Ke Qiu Hailong Yan Lei Dai Tailored amination enables switchable synthesis of α- and γ-amino acid derivatives from extended quinone methides Nature Communications |
| title | Tailored amination enables switchable synthesis of α- and γ-amino acid derivatives from extended quinone methides |
| title_full | Tailored amination enables switchable synthesis of α- and γ-amino acid derivatives from extended quinone methides |
| title_fullStr | Tailored amination enables switchable synthesis of α- and γ-amino acid derivatives from extended quinone methides |
| title_full_unstemmed | Tailored amination enables switchable synthesis of α- and γ-amino acid derivatives from extended quinone methides |
| title_short | Tailored amination enables switchable synthesis of α- and γ-amino acid derivatives from extended quinone methides |
| title_sort | tailored amination enables switchable synthesis of α and γ amino acid derivatives from extended quinone methides |
| url | https://doi.org/10.1038/s41467-025-60749-7 |
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