The bioorthogonal chemical reporter strategy is emerging as a versatile method for the labeling of biomolecules, such as nucleic acids, lipids, carbohydrates, and proteins. In this approach, an abiotic chemical functionality (reporter) is incorporated into a target biomolecule and can then react with a complementary bioorthogonal functional group linked to one of a diverse set of probes. The az...

Specific and highly efficient fluorescent labeling techniques for biomolecules, especially for proteins, are required for the quantitative analyses of bio-phenomena and for subsequent systems biology. Although expression of exogenous proteins fused with fluorescent tags, such as green fluorescent protein, is the most widely used method for quantitative bio-analysis, the following problems need ...

Chemical reactions that enable selective biomolecule labeling in living organisms offer a means to probe biological processes in vivo. Very few reactions possess the requisite bioorthogonality, and, among these, only the Staudinger ligation between azides and triarylphosphines has been employed for direct covalent modification of biomolecules with probes in the mouse, an important model organis...

The discovery of biocompatible reactions had a tremendous impact on chemical biology, allowing the study of numerous biological processes directly in complex systems. However, despite the fact that multiple biocompatible reactions have been developed in the past decade, very few work well in living mice. Here we report that D-cysteine and 2-cyanobenzothiazoles can selectively react with each ot...

A convenient synthesis of novel bi/tricyclic azasugars fused thiazolidin-4-one and thiazinan-4-one by the one-pot tandem Staudinger/aza-Wittig/cyclization reaction under microwave radiation was demonstrated. The reactions were carried out with the azidosugar 1 and mercaptan acids via a key intermediate Schiff base and stereoselectively afforded the titled bi/tricyclic azasugars in good yield. A...

Organic azides are well-established as versatile compounds that can act as precursors of different heterocycles (triazoles, triazolines, tetrazoles, etc.) or other nitrogen-containing compounds, such as amines (Staudinger reduction, Curtius rearrangement) or imines (Schmidt rearrangement, aza-Wittig reaction). Besides the ubiquitous copper-catalysed azide–alkyne cycloaddition reaction, two appl...

The review reports a short biography of the Italian naturalized chemist Hugo Schiff and an outline on the synthesis and use of his most popular discovery: the imines, very well known and popular as Schiff Bases. Recent developments on their "metallo-imines" variants have been described. The applications of Schiff bases in organic synthesis as partner in Staudinger and hetero Diels-Alder reactio...

Chemoselective conjugation of an azido-functionalized thrombomodulin to pancreatic islets was achieved by Staudinger ligation to a surface-bound bifunctional poly(ethylene glycol) linker. The presence of the tethered thrombomodulin resulted in a significant increase in the production of activated protein C with a reduction in islet-mediated thrombogenicity. This report highlights the potential ...