Triple Bioorthogonal Ligation Strategy for Simultaneous Labeling of Multiple Enzymatic Activities

Willems, Lianne I.; Li, Nan; Florea, Bogdan I.; Ruben, Mark; Marel, Gijsbert A. van der; Overkleeft, Herman S.

doi:10.1002/anie.201200923

Cited by 110 publications

(98 citation statements)

References 43 publications

(38 reference statements)

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“…50 Despite this possible unwanted side reactions, it was recently described that the DAR inv can be used as an orthogonal ligation technique to the copper-free azide− alkyne [3 + 2] cycloaddition 29 and the CuAAC. 51 We observed no side reaction in all our intermediate products and the final product. By MALDI-ToF-MS after SPPS of the DAR inv precursor diene−highSP−Pra, no side reaction between the tetrazine and the alkyne bearing C-terminal Pra of highSP−Pra was detected.…”

Section: ■ Resultsmentioning

confidence: 56%

Biocompatible Silicon Surfaces through Orthogonal Click Chemistries and a High Affinity Silicon Oxide Binding Peptide

et al. 2012

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Multifunctionality is gaining more and more importance in the field of improved biomaterials. Especially peptides feature a broad chemical variability and are versatile mediators between inorganic surfaces and living cells. Here, we synthesized a unique peptide that binds to SiO(2) with nM affinity. We equipped the peptide with the bioactive integrin binding c[RGDfK]-ligand and a fluorescent probe by stepwise Diels-Alder reaction with inverse electron demand and copper(I) catalyzed azide-alkyne cycloaddition. For the first time, we report the generation of a multifunctional peptide by combining these innovative coupling reactions. The resulting peptide displayed an outstanding binding to silicon oxide and induced a significant increase in cell spreading and cell viability of osteoblasts on the oxidized silicon surface.

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Section: ■ Resultsmentioning

confidence: 56%

Biocompatible Silicon Surfaces through Orthogonal Click Chemistries and a High Affinity Silicon Oxide Binding Peptide

et al. 2012

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“…41 While the authors were able to perform the three ''click'' reactions in parallel, practical reasons (background fluorescence due to CuSO 4 and a poor signal-to-noise ratio when SPAAC was applied) finally led to a multistep protocol. 3.3.1 iEDDA in materials and polymer science.…”

Section: View Article Onlinementioning

confidence: 99%

Inverse electron demand Diels–Alder (iEDDA)-initiated conjugation: a (high) potential click chemistry scheme

2013

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Inverse electron demand Diels-Alder reactions (iEDDA) between 1,2,4,5-tetrazines and olefins have emerged into a state-of-the art concept for the conjugation of biomolecules. Now, this reaction is also increasingly being applied in polymer science and materials science. The orthogonality of this exciting reaction to other well-established click chemistry schemes, its high reaction speed and its biocompatibility are key features of iEDDA making it a powerful alternative to existing ligation chemistries. The intention of this tutorial review is to introduce the reader to the fundamentals of inverse electron demand Diels-Alder additions and to answer the question whether iEDDA chemistry is living up to the criteria for a ''click'' reaction and can serve as a basis for future applications in postsynthetic modification of materials. Key learning points(1) Electron-rich dienophiles and electron-poor dienes (e.g. tetrazines) react in an inverse electron demand Diels-Alder reaction (iEDDA).(2) iEDDA fulfils Sharpless' criteria for a ''click'' reaction while offering advantages over already established ''click'' chemistry schemes.

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“…[83] Similarly, Overkleeft and colleagues recently reported a triple bioorthogonal strategy for simultaneous labeling of multiple enzymatic activities. [84] It is of enormous interest to see how these recent ABPP innovations will evolve and expand to provide discerning insights into our understanding of protein function. By now, the merits from these innovative developments are already evident.…”

Section: Discussionmentioning

confidence: 99%

Activity‐Based Protein Profiling: Recent Advances in Probe Development and Applications

Yang

2015

ChemBioChem

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The completion of the human genome sequencing project has provided a wealth of new information regarding the genomic blueprint of the cell. Although, to date, there are roughly 20,000 genes in the human genome, the functions of only a handful of proteins are clear. The major challenge lies in translating genomic information into an understanding of their cellular functions. The recently developed activity-based protein profiling (ABPP) is an unconventional approach that is complementary for gene expression analysis and an ideal utensil in decoding this overflow of genomic information. This approach makes use of synthetic small molecules that covalently modify a set of related proteins and subsequently facilitates identification of the target protein, enabling rapid biochemical analysis and inhibitor discovery. This tutorial review introduces recent advances in the field of ABPP and its applications.

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Triple Bioorthogonal Ligation Strategy for Simultaneous Labeling of Multiple Enzymatic Activities

Cited by 110 publications

References 43 publications

Biocompatible Silicon Surfaces through Orthogonal Click Chemistries and a High Affinity Silicon Oxide Binding Peptide

Biocompatible Silicon Surfaces through Orthogonal Click Chemistries and a High Affinity Silicon Oxide Binding Peptide

Inverse electron demand Diels–Alder (iEDDA)-initiated conjugation: a (high) potential click chemistry scheme

Activity‐Based Protein Profiling: Recent Advances in Probe Development and Applications

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