Diazirine

Last updated
Diazirine
Diazirin - Diazirine.svg
3H-Diazirine-3D-balls.png
Identifiers
3D model (JSmol)
605387
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/CH2N2/c1-2-3-1/h1H2
    Key: GKVDXUXIAHWQIK-UHFFFAOYSA-N
  • 3H:C1N=N1
Properties
CH2N2
Molar mass 42.041 g·mol−1
Related compounds
Related compounds
1H-Diazirine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
A generic diazirine Diazirines.svg
A generic diazirine

In organic chemistry, diazirines are a class of organic molecules consisting of a carbon bound to two nitrogen atoms, which are double-bonded to each other, forming a cyclopropene-like ring, 3H-diazirine (>CN2). They are isomeric with diazocarbon groups (>C=N=N), and like them can serve as precursors for carbenes by loss of a molecule of dinitrogen. For example, irradiation of diazirines with ultraviolet light leads to carbene insertion into various C−H , N−H, and O−H bonds. [1] Hence, diazirines have grown in popularity as small, photo-reactive, crosslinking reagents. [2] They are often used in photoaffinity labeling studies to observe a variety of interactions, including ligand-receptor, ligand-enzyme, protein-protein, and protein-nucleic acid interactions. [3]

Contents

Synthesis

A number of methods exist in the literature for the preparation of diazirines, which begin from a variety of reagents. [4]

Synthesis from ketones

Generally, synthetic schemes that begin with ketones (>C=O) involve conversion of the ketone with the desired substituents to diaziridines (>CN2H2). These diaziridenes are then subsequently oxidized to form the desired diazirines.

Diaziridines can be prepared from ketones by oximation, followed by tosylation (or mesylation), and then finally by treatment with ammonia (NH3). Generally, oximation reactions are performed by reacting the ketone with hydroxylammonium chloride (NH3OH−Cl+) under heat in the presence of a base such as pyridine. [5] [6] Subsequent tosylation or mesylation of the alpha-substituted oxygen with tosyl or mesyl chloride in the presence of base yields the tosyl or mesyl oxime. [7] The final treatment of the tosyl or mesyl oxime with ammonia produces the diaziridine. [1] [3] [7] [8]

Generic diaziridine synthesis by oximation, tosylation, and treatment with ammonia. Screen Shot 2015-12-01 at 12.35.12 PM .png
Generic diaziridine synthesis by oximation, tosylation, and treatment with ammonia.

Diaziridines can be also produced directly by the reaction of ketones with ammonia in the presence of an aminating agent such as a monochloramine or hydroxyl amine O-sulfonic acid. [9]

Diaziridines can be oxidized to diazirines by a number of methods. These include oxidation by chromium-based reagents such as the Jones oxidation, [10] oxidation by iodine and triethylamine, [5] oxidation by silver oxide, [11] oxidation by oxalyl chloride, [7] or even electrochemical oxidation on a platinum-titanium anode. [12]

Jones oxidation of a generic diaziridine to a diazirine. Screen Shot 2015-12-01 at 7.51.23 PM.png
Jones oxidation of a generic diaziridine to a diazirine.

Synthesis by Graham reaction

Diazirines can be alternatively formed in a one-pot process using the Graham reaction, starting from amidines. [13] This reaction yields a halogenated diazirine, whose halogen can be displaced by various nucleophilic reagents. [14]

Graham-reaction-2D-scheme.svg
The Graham reaction as a method of diazirine synthesis, where X = Cl or Br.
Diazirine Exchange screenshot.png
The diazirine exchange reaction using various anions and the counterion tetra-n-butylammonium.

Chemistry

Upon irradiation with UV light, diazirines form reactive carbene species. The carbene may exist in the singlet form, in which the two free electrons occupy the same orbital, or the triplet form, with two unpaired electrons in different orbitals.

Diazirines can be decomposed by using UV-light. Diazirines decomposition.svg
Diazirines can be decomposed by using UV-light.

Triplet vs singlet carbene products

The substituents on the diazirine affect which carbene species is generated upon irradiation and subsequent photolytic cleavage. Diazirine substituents that are electron donating in nature can donate electron density to the empty p-orbital of the carbene that will be formed, and hence can stabilize the singlet state. For example, phenyldiazirine produces phenylcarbene in the singlet carbene state [15] whereas p-nitrophenylchlorodiazirine or trifluorophenyldiazirine produce the respective triplet carbene products. [16] [17]

Electron donating substituents can also encourage photoisomerization to the linear diazo compound [30], rather than the singlet carbene, and hence these compounds are unfavorable for use in biological assays. [18] On the other hand, trifluoroaryldiazirines in particular show favorable stability and photolytic qualities [18] and are most commonly used in biological applications. [1]

Three diazirines are shown above. Phenyldiazirine produces the singlet carbene whereas trifluoromethylphenyldiazirine and p-nitrophenylchlorodiazirine produce triplet state carbenes. Screen Shot 2015-12-01 at 3.56.20 PM.png
Three diazirines are shown above. Phenyldiazirine produces the singlet carbene whereas trifluoromethylphenyldiazirine and p-nitrophenylchlorodiazirine produce triplet state carbenes.

Carbenes produced from diazirines are quickly quenched by reaction with water molecules, [19] and hence yields for photoreactive crosslinking assays are often low. Yet, as this feature minimizes unspecific labeling, it is actually an advantage of using diazirines.

Use in photoreactive crosslinking

Diazirines are often used as photoreactive crosslinking reagents, as the reactive carbenes they form upon irradiation with UV light can insert into C-H, N-H, and O-H bonds. This results in proximity dependent labeling of other species with the diazirine containing compound.

Diazirines are often preferred to other photoreactive crosslinking reagents due to their smaller size, longer irradiation wavelength, short period of irradiation required, and stability in the presence of various nucleophiles, and in both acidic and basic conditions. [20] Benzophenones, which form reactive triplet carbonyl species upon irradiation, often require long periods of irradiation which can result in non-specific labeling, and moreover are often inert to various polar solvents. [21] Aryl azides require a low wavelength of irradiation, which can damage the biological macromolecules under investigation.

Examples in receptor labeling studies

Diazirines are widely used in receptor labeling studies. This is because diazirine-containing analogs of various ligands can be synthesized and incubated with their respective receptors, and then subsequently exposed to light to produce reactive carbenes. The carbene will covalently bond to residues in the binding site of the receptor. The carbene compound may include a bioorthogonal tag or handle by which the protein of interest can be isolated. The protein can then be digested and sequenced by mass spectrometry in order to identify which residues the carbene containing ligand is bound to, and hence the identity of the binding site in the receptor.

Examples of diazirines used in receptor labeling studies include:

Brassinosteroid diazirine analog.jpg
Propofol.svg
M-Azipropofol.png
Propofol (left) and m-azipropofol, a diazirine analog of it

Examples in enzyme-substrate studies

In a manner analogous to receptor labeling, diazirine containing compounds that are analogs of natural substrates have also been used to identify binding pockets of enzymes. Examples include:

Examples in nucleic acid studies

Diazirines have been used in photoaffinity labeling experiments involving nucleic acids as well. Examples include:

1-s2.0-S0968089611005062-gr39.jpg

Diazirines have also been used to study protein lipid interactions, for example the interaction of various sphingolipids with proteins in vivo. [29]

Related Research Articles

<span class="mw-page-title-main">Benzophenone</span> Chemical compound

Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. It is a white solid that is soluble in organic solvents. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone.

<span class="mw-page-title-main">Enamine</span> Class of chemical compounds

An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates.

<span class="mw-page-title-main">Cross-link</span> Bonds linking one polymer chain to another

In chemistry and biology a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural polymers.

In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is R−:C−R' or R=C: where the R represents substituents or hydrogen atoms.

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<span class="mw-page-title-main">Oxaziridine</span> Chemical compound

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<span class="mw-page-title-main">Graham reaction</span>

In organic chemistry, the Graham reaction is an oxidation reaction that converts an amidine into a diazirine using a hypohalite reagent. The halide of the hypohalite oxidant, or another similar anionic additive to the reaction, is retained as a substituent on the diazirine product. The reaction was first reported in 1965. Various reaction mechanisms have been proposed.

<i>m</i>-Terphenyl Organic ligand

m-Terphenyls (also known as meta-terphenyls, meta-diphenylbenzenes, or meta-triphenyls) are organic molecules composed of two phenyl groups bonded to a benzene ring in the one and three positions. The simplest formula is C18H14, but many different substituents can be added to create a diverse class of molecules. Due to the extensive pi-conjugated system, the molecule it has a range of optical properties and because of its size, it is used to control the sterics in reactions with metals and main group elements. This is because of the disubstituted phenyl rings, which create a pocket for molecules and elements to bond without being connected to anything else. It is a popular choice in ligand, and the most chosen amongst the terphenyls because of its benefits in regards to sterics. Although many commercial methods exist to create m-terphenyl compounds, they can also be found naturally in plants such as mulberry trees.

References

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