Abstract
The development of bioorthogonal reactions is expected to propel further advances in chemical biology. In this study, we demonstrate Staudinger-Diels-Alder (SDA) ligation as a candidate for a new bioorthogonal reaction. This reaction ligates two molecules via strong C-C bonds at room temperature. We found that the aryl substituent of azide-benzocyclobutene (azide-BCB) had a strong influence on the molecule’s tolerance to water. In particular, Cl-substituted azide-BCBs generated the ligated product in high yield, even in the presence of water. Mechanistic investigations using DFT methods revealed that hydrophobic electron-withdrawing substituents suppressed the side reactions of SDA ligation.
Original language | English |
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Pages (from-to) | 1501-1506 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 90 |
Issue number | 4 |
DOIs | |
State | Published - 2025/01/31 |
ASJC Scopus subject areas
- Organic Chemistry