The Staudinger Ligation

Nieto-García, Olaia; Jaffee, Marcie B.; Mühlberg, Michaela; Hackenberger, Christian P. R.

doi:10.1002/9783527683451.ch4

Cited by 7 publications

(6 citation statements)

References 59 publications

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“…The Staudinger ligation (Scheme 2A), traceless-Staudinger ligation (Scheme 2B) and Staudinger-phosphite/phosphonite reactions exploit the reaction between azides and trivalent-phosphine reagents to form stable amide bonds. 72 As one of the earliest developed bioorthogonal reactions, the Staudinger ligation has been successfully utilized in both in vitro and in vivo applications. 73 However, the utility of these reactions is largely limited by their slow reaction rate and the oxidation propensity of the requisite phosphine reagents.…”

Section: Chemistry On Proteinsmentioning

confidence: 99%

Recent progress in enzymatic protein labelling techniques and their applications

et al. 2018

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Protein-based conjugates are valuable constructs for a variety of applications. Conjugation of proteins to fluorophores is commonly used to study their cellular localization and the protein-protein interactions. Modification of therapeutic proteins with either polymers or cytotoxic moieties greatly enhances their pharmacokinetics and potency. To label a protein of interest, conventional direct chemical reaction with the side-chains of native amino acids often yields heterogeneously modified products. This renders their characterization complicated, requires difficult separation steps and may impact protein function. Although modification can also be achieved via the insertion of unnatural amino acids bearing bioorthogonal functional groups, these methods can have lower protein expression yields, limiting large scale production. As a site-specific modification method, enzymatic protein labelling is highly efficient and robust under mild reaction conditions. Significant progress has been made over the last five years in modifying proteins using enzymatic methods for numerous applications, including the creation of clinically relevant conjugates with polymers, cytotoxins or imaging agents, fluorescent or affinity probes to study complex protein interaction networks, and protein-linked materials for biosensing. This review summarizes developments in enzymatic protein labelling over the last five years for a panel of ten enzymes, including sortase A, subtiligase, microbial transglutaminase, farnesyltransferase, N-myristoyltransferase, phosphopantetheinyl transferases, tubulin tyrosin ligase, lipoic acid ligase, biotin ligase and formylglycine generating enzyme.

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Section: Chemistry On Proteinsmentioning

confidence: 99%

Recent progress in enzymatic protein labelling techniques and their applications

et al. 2018

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“…Finally, the applicability of the method was further demonstrated through the synthesis of tetramer 74 (Scheme 28, depicted in the frame, synthesized in N→C fashion). 74 Scheme 28 Peptide synthesis via CDI activation of an amine (top) with selected examples (bottom) 74 Broadening on the traceless Staudinger ligation, 75 where an azide 75 acts as amine surrogate, Ashfeld and co-workers developed a chemoselective Oto N-acyl migration using a chlorophosphite as a dual activation agent. 76 The reaction proceeds via an intermediate ester azaylide 76 formed from the reaction of a preactivated carboxylic acid with a bisfunctional chlorophosphite and an azide.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

A New Wave of Amide Bond Formations for Peptide Synthesis

2019

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The construction of peptidic amide bonds has become a daily laboratory practice by virtue of well-established ‘coupling reagents’. Nonetheless, inherent limitations connected to these classical coupling methods in terms of waste, safety and expense have yet to be conquered. Research efforts have been devoted to synthetic methods able to surpass these limitations. This short review focuses on the advances made in these ‘non-classical’ methods for amide bond formation with a specific application in peptide chemistry. It consists of two main sections: (i) novel carboxylic activation reagents, and (ii) carboxylic acid and amine surrogates.1 Introduction2 Alternative Carboxylic acid Activation Reagents3 Carboxylic Acid and Amine Surrogates4 Conclusion and Perspectives

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“…In addition, the azide group can take part in versatile transformations. For instance, it can be used for direct synthesis of amines, in Staudinger ligation, in the synthesis of phosphazene for aza-Wittig reaction, and as the precursor of nitrene . Among various synthetic approaches, azidation of alkenes (azido-functionalization of alkenes) is particularly attractive on account of the direct installation of azide on the readily available carbon–carbon double bonds.…”

Section: Introductionmentioning

confidence: 99%

Iron-Catalyzed Asymmetric Haloazidation of α,β-Unsaturated Ketones: Construction of Organic Azides with Two Vicinal Stereocenters

et al. 2017

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Organic azides play important roles in synthetic chemistry, chemical biology, drug discovery, and material science. Azido-functionalization of alkenes is one of the most efficient procedures for rapid introduction of azide group into organic compounds. But only a few examples have been documented in the catalytic asymmetric version of the azidation of alkenes. Herein, we report an unprecedented highly diastereo- and enantioselective bromoazidation of α,β-unsaturated ketones catalyzed by chiral N,N'-dioxide/Fe(OTf) complexes. An array of aryl, heteroaryl, and alkyl substituted α,β-unsaturated ketones were transformed to the corresponding α-bromo-β-azido ketones in high yields with excellent diastereo- and enantioselectivities. The catalytic system was also applicable for chloroazidation and iodoazidation of chalcone. Kinetic studies and some control experiments suggested that the reaction might proceed via a 1,4-addition/halogenation pathway.

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The Staudinger Ligation

Cited by 7 publications

References 59 publications

Recent progress in enzymatic protein labelling techniques and their applications

Recent progress in enzymatic protein labelling techniques and their applications

A New Wave of Amide Bond Formations for Peptide Synthesis

Iron-Catalyzed Asymmetric Haloazidation of α,β-Unsaturated Ketones: Construction of Organic Azides with Two Vicinal Stereocenters

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