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The Furan–Thiol–Amine Reaction Facilitates DNA-Compatible Thiopyrrole-Grafted Macrocyclization and Late-Stage Amine Transformation
We here report an efficient DNA-compatible furan–thiol–amine reaction for macrocyclization and late-stage amine transformation. This reaction, conducted under mild conditions, enables the facile cyclization of DNA-conjugated linear peptides into thiopyrrole-grafted macrocycles regardless of ring siz...
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| Published in: | Organic letters 2025-01, Vol.27 (1), p.498-503 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-a225t-995e26b0594a7a6a76c027fd5e1210458926659fccb134ab6cee3096d3d23d653 |
| container_end_page | 503 |
| container_issue | 1 |
| container_start_page | 498 |
| container_title | Organic letters |
| container_volume | 27 |
| creator | Nie, Qigui Xu, Tingting Fang, Xianfu Dan, Yanrong Zhang, Gong Li, Yangfeng Li, Jianbo Li, Yizhou |
| description | We here report an efficient DNA-compatible furan–thiol–amine reaction for macrocyclization and late-stage amine transformation. This reaction, conducted under mild conditions, enables the facile cyclization of DNA-conjugated linear peptides into thiopyrrole-grafted macrocycles regardless of ring size or side-chain modification with good to excellent conversion yields. Additionally, this strategy was employed for the late-stage transformation of terminal amines, serving as critical intermediates in the construction of DNA-encoded peptide libraries. Diverse amines were successfully converted into their corresponding thiopyrrole scaffolds, thereby expanding the structural diversity that can be achieved within DNA-encoded libraries. |
| doi_str_mv | 10.1021/acs.orglett.4c04505 |
| format | article |
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| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2025-01, Vol.27 (1), p.498-503 |
| issn | 1523-7060 1523-7052 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_3149538733 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Amines - chemistry Cyclization DNA - chemistry Furans - chemistry Molecular Structure Peptide Library Peptides - chemical synthesis Peptides - chemistry Pyrroles - chemistry Sulfhydryl Compounds - chemistry |
| title | The Furan–Thiol–Amine Reaction Facilitates DNA-Compatible Thiopyrrole-Grafted Macrocyclization and Late-Stage Amine Transformation |
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