DNA Conjugation by Staudinger Ligation

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. Finally, the method is compared to other bioorthogonal labeling methods.

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“…191,134,173 Conjugation with modified phosphanes 41 yielded biotin-labeled DNA 42. 190 A brief overview of this application is shown in Scheme 9.…”

Section: Staudinger Ligation For Labeling Of Biomoleculesmentioning

confidence: 99%

The Staudinger Ligation

et al. 2020

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“…In the field of DNA conjugation, Marx and coworkers reported on a DNA polymerase-supported introduction of azide-modified triphosphates 50, 84 which can be smoothly conjugated via azides 51 with modified phosphines 52, furnishing labelled DNA 53, for example with biotin for further detection as described in the biotin labelling section (Scheme 10). 85 On the other hand, fluorescent labelling at the 5 0 terminus of DNA 75 and methyltransferasemediated DNA labelling 86 can also be performed by Staudinger ligation.…”

Section: Applications In Biology 41 Labelling Of Dnamentioning

confidence: 99%

“…83 Scheme 10 DNA labelling of azido-modified dATP with biotin (B). 84,85 to the extent of total chemical synthesis of proteins. The native chemical ligation results in the generation of a final peptide of the type represented by 57 (Scheme 11A).…”

Section: Peptide-peptide Conjugationsmentioning

confidence: 99%

Bioconjugation via azide–Staudinger ligation: an overview

et al. 2011

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“…By introducing an electrophilic reactive group within the phosphine molecule, an intramolecular cyclization reaction can outcompete hydrolysis to yield an amide‐linked product (Scheme a). The Staudinger ligation has been employed in many applications, ranging from the fluorescent labeling of proteins62 and DNA,63 the immobilization of proteins to surfaces,30, 64 labeling of cell‐surface glycoproteins,65, 66–68 and activity‐based proteosome profiling,69–71 among others (for a comprehensive review, see Refs. 31, 72).…”

Section: Chemoselective Ligation Reactionsmentioning

confidence: 99%

Chemoselective ligation techniques: Modern applications of time‐honored chemistry

Tiefenbrunn¹,

Dawson²

2010

Biopolymers

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Chemoselective ligation techniques enable the selective modification of proteins and other biomolecules in dilute aqueous solution. Importantly, these reactions occur at or near physiological pH and are compatible with the complex array of functional groups commonly found in biological macromolecules including proteins, nucleotides, and carbohydrates, allowing conjugation reactions to be carried out on unprotected substrates. Recently, a growing number of reactions with established utility in synthetic organic chemistry have been shown to have surprising utility in the context of biological molecules in aqueous media. In this review we highlight several promising reactions that may have widespread applicability in the generation of new materials based on biological macromolecules.

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DNA Conjugation by Staudinger Ligation

Abstract: Two 5 modified 2'-deoxyuridin triphosphates and a 7 modified 2'-deoxy-7-deazaadenosine were synthesized carrying a terminal azide linked to the base.

Cited by 13 publications

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The Staudinger Ligation

The Staudinger Ligation

Bioconjugation via azide–Staudinger ligation: an overview

Chemoselective ligation techniques: Modern applications of time‐honored chemistry

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