Jump to main content
Jump to site search


The one-pot nonhydrolysis Staudinger reaction and Staudinger or SPAAC ligation

Author affiliations

Abstract

The combined usage of two bioorthogonal reactions can provide hetero-bifunctional molecules under physiological conditions for various applications. Based on the Nonhydrolysis Staudinger Reaction (NSR), we design and develop a bisazido linker 1 for chemoselective dual-functionalization without the need of protection using catalyst-free and one-pot procedures. The NSR is much faster with tetrafluorinated aromatic azide than that the Staudinger–Bertozzi or SPAAC ligation with alkyl azide, as revealed by HPLC analysis and fluorescence kinetics. Based on the tandem NSR and Staudinger–Bertozzi ligation, we prepare a molecular beacon 7 from 1 in one-pot synthesis with a recovery yield of 32%. When a faster SPAAC ligation is used instead of the Staudinger–Bertozzi ligation, compound 8 is prepared in the tandem NSR and SPAAC reactions with a recovery yield of 59%. As a proof-of-concept study, the tandem NSR and SPAAC ligation is further used to produce a FRET-based dyad in living cells, as revealed by dual-color bioimaging. This work shows that NSR can be combined with other bioorthogonal reactions without the need of protection in one-pot.

Graphical abstract: The one-pot nonhydrolysis Staudinger reaction and Staudinger or SPAAC ligation

Back to tab navigation

Supplementary files

Publication details

The article was received on 04 Mar 2019, accepted on 09 Apr 2019 and first published on 10 Apr 2019


Article type: Communication
DOI: 10.1039/C9OB00528E
Citation: Org. Biomol. Chem., 2019, Advance Article

  •   Request permissions

    The one-pot nonhydrolysis Staudinger reaction and Staudinger or SPAAC ligation

    L. Cheng, X. Kang, D. Wang, Y. Gao, L. Yi and Z. Xi, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00528E

Search articles by author

Spotlight

Advertisements