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Hu P, Feng T, Yeung CC, et al. A Photo-Triggered Traceless Staudinger-Bertozzi Ligation Reaction. Chemistry. 2016;22(33):11537-42doi: 10.1002/chem.201601807.
Hu, P., Feng, T., Yeung, C. C., Koo, C. K., Lau, K. C., & Lam, M. H. (2016). A Photo-Triggered Traceless Staudinger-Bertozzi Ligation Reaction. Chemistry (Weinheim an der Bergstrasse, Germany), 22(33), 11537-42. https://doi.org/10.1002/chem.201601807
Hu, Peng, et al. "A Photo-Triggered Traceless Staudinger-Bertozzi Ligation Reaction." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,33 (2016): 11537-42. doi: https://doi.org/10.1002/chem.201601807
Hu P, Feng T, Yeung CC, Koo CK, Lau KC, Lam MH. A Photo-Triggered Traceless Staudinger-Bertozzi Ligation Reaction. Chemistry. 2016 Aug 08;22(33):11537-42. doi: 10.1002/chem.201601807. Epub 2016 Jul 07. PMID: 27123884.
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Chemistry. 2016 Aug 08;22(33):11537-42. doi: 10.1002/chem.201601807. Epub 2016 Jul 07.

A Photo-Triggered Traceless Staudinger-Bertozzi Ligation Reaction.

Chemistry (Weinheim an der Bergstrasse, Germany)

Peng Hu, Tianshi Feng, Chi-Chung Yeung, Chi-Kin Koo, Kai-Chung Lau, Michael H W Lam

Affiliations

  1. Department of Chemistry and Biology, City University of Hong Kong, 83 Tat Chee Avenue, Hong Kong SAR, China.
  2. Advanced Laboratory for Environmental Research & Technology, USTC-CityU, Suzhou, China.
  3. CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui, 230026, China.
  4. Department of Chemistry and Biology, City University of Hong Kong, 83 Tat Chee Avenue, Hong Kong SAR, China. [email protected].

PMID: 27123884 DOI: 10.1002/chem.201601807

Abstract

The use of light to control the course of a chemical/biochemical reaction is an attractive idea because of its ease of administration with high precision and fine spatial resolution. Staudinger ligation is one of the commonly adopted conjugation processes that involve a spontaneous reaction between azides and arylphosphines to form iminophosphoranes, which further hydrolyze to give stable amides. We designed an anthracenylmethyl diphenylphosphinothioester (1) that showed promising Staudinger ligation reactivity upon photo-excitation. Broadband photolysis at 360-400 nm in aqueous organic solvents induced heterolytic cleavage of its anthracenylmethyl-phosphorus bond, releasing a diphenylphosphinothioester (2) as an efficient traceless Staudinger-Bertozzi ligation reagent. The quantum yield of such a photo-induced heterolytic bond-cleavage at the optimal wavelength of photolysis (376 nm) at room temperature is ≥0.07. This work demonstrated the feasibility of photocaging arylphosphines to realize the photo-triggering of the Staudinger ligation reaction.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Staudinger-Bertozzi ligation; conjugation reaction; phosphonium salt; photo-triggering; photolysis

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