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The Staudinger Ligation

Bednarek, C. 1; Wehl, I. 1; Jung, N. 1; Schepers, U. 1,2; Bräse, S. 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)
2 Institut für Funktionelle Grenzflächen (IFG), Karlsruher Institut für Technologie (KIT)


While the Staudinger reaction has first been described a hundred years ago in 1919, the ligation reaction became one of the most important and efficient bioconjugation techniques in the 1990s and this century. It holds the crucial characteristics for bioorthogonal chemistry: biocompatibility, selectivity, and a rapid and high-yielding turnover for a wide variety of applications. In the past years, it has been used especially in chemical biology for peptide/protein synthesis, posttranslational modifications, and DNA labeling. Furthermore, it can be used for cell-surface engineering, development of microarrays, and drug delivery systems. However, it is also possible to use the reaction in synthetic chemistry for general formation of amide bonds. In this review, the three major types, traceless and nontraceless Staudinger Ligation as well as the Staudinger phosphite reaction, are described in detail. We will further illustrate each reaction mechanism and describe characteristic substrates, intermediates, and products. In addition, not only its advantages but also stereochemical aspects, scope, and limitations, in particular side reactions, are discussed. ... mehr

Postprint §
DOI: 10.5445/IR/1000119621
Veröffentlicht am 14.06.2022
DOI: 10.1021/acs.chemrev.9b00665
Zitationen: 129
Web of Science
Zitationen: 118
Zitationen: 135
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Funktionelle Grenzflächen (IFG)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2020
Sprache Englisch
Identifikator ISSN: 0009-2665, 1520-6890
KITopen-ID: 1000119621
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in Chemical reviews
Verlag American Chemical Society (ACS)
Band 120
Heft 10
Seiten 4301–4354
Vorab online veröffentlicht am 01.05.2020
Nachgewiesen in Dimensions
Web of Science
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