Water-Compatible Staudinger-Diels-Alder Ligation

Masaru Tanioka*, Shohei Kanayama, Fumino Kitamura, Akinari Takano, Yukiko Ikeda, Aki Kohyama, Tsuyoshi Yamada, Yuji Matsuya*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

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 languageEnglish
Pages (from-to)1501-1506
Number of pages6
JournalJournal of Organic Chemistry
Volume90
Issue number4
DOIs
StatePublished - 2025/01/31

ASJC Scopus subject areas

  • Organic Chemistry

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