Amine-reactive chemical groups in biomolecular probes for labeling and crosslinking primary amines include NHS esters (N-hydroxysuccinimide esters) and imidoesters. This article describes the reaction chemistries and biology applications of this class of reagents.

In aerobic organisms like humans, isothiocyanates are detoxified by conjugation with glutathione (GSH), which converts the electrophile to a dithiocarbamate in a conjugation reaction catalyzed by glutathione transferases (GSTs).

Functional, micropatterned and multicomponent polymer brush surfaces can be rapidly fabricated via base-catalyzed thiol –isocyanate “click” reactions. Applications for advanced functional polymeric surfaces that possess precisely engineered properties are expanding rapidly.

In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%).

Second reaction is nucleophilic addition of thiol to isothiocyanate (need catalytic amount of base, so cysteine in salt form. Product is dithiocarbamate, deprotection by acid.

The reaction between an azide and an alkyne either using a copper catalyst or a copper free strained alkyne results in the formation of a stable triazole linkage between the coupling partners. This reaction has received much attention due to the bioorthogonal nature of …

Modification of aromatic amines requires a highly reactive reagent, such as an isocyanate, isothiocyanate, sulfonyl chloride or acid halide, but can be done at any pH above ~4. A tyrosine residue can be selectively modified to form an o -aminotyrosine aromatic amine, which can then be reacted at a relatively low pH with certain amine-reactive ...

Fluorescein-5-isothiocyanate (FITC) modeling produced a Deff range of 1E-20 to 5E-20 cm2/s at a 1 µm cell monolayer thickness and a Deff constant near 5E-29 cm2/s at a 5 µm cell monolayer...

Thiol groups reacted by far more readily than amino groups. A specific effect was observed with cysteine, indicating an intramolecular transfer of the fluorescein residue from SH to NH2. With sarcoplasmic vesicles both types of reactions were observed.

The reaction of isothiocyanates with compounds carrying an active hydrogen give adducts which undergo cyclization spontaneously or by addition of external reagents to yield heterocycles.