Staudinger ligation as a method for bioconjugation

Sander S. van Berkel, M.B. van Eldijk, J.C.M. Hest, van

Research output: Contribution to journalReview articleAcademicpeer-review

181 Citations (Scopus)

Abstract

In 1919 the German chemist Hermann Staudinger was the first to describe the reaction between an azide and a phosphine. It was not until recently, however, that Bertozzi and co-workers recognized the potential of this reaction as a method for bioconjugation and transformed it into the so-called Staudinger ligation. The bio-orthogonal character of both the azide and the phosphine functions has resulted in the Staudinger ligation finding numerous applications in various complex biological systems. For example, the Staudinger ligation has been utilized to label glycans, lipids, DNA, and proteins. Moreover, the Staudinger ligation has been used as a synthetic method to construct glycopeptides, microarrays, and functional biopolymers. In the emerging field of bio-orthogonal ligation strategies, the Staudinger ligation has set a high standard to which most of the new techniques are often compared. This Review summarizes recent developments and new applications of the Staudinger ligation. Phosphorus and azides have a high affinity for one another. This discovery has led to the development of various phosphorus-containing bioconjugation probes. At present, traceless, nontraceless, and phosphite Staudinger ligation probes are frequently applied. The current status of their utilization in life sciences and materials science is described in this Review.

Original languageEnglish
Pages (from-to)8806-8827
Number of pages22
JournalAngewandte Chemie - International Edition
Volume50
Issue number38
DOIs
Publication statusPublished - 12 Sep 2011
Externally publishedYes

Keywords

  • azides
  • bioconjugation
  • chemoselective reactions
  • labeling
  • Staudinger ligation

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