Clickable 19F NMR Probes
| Cat. # | Quantity | Price | Lead time | Buy this product |
|---|---|---|---|---|
| CFKIT_FAZ02 | 1 kit | 1.499,00 € | in stock |
- Name: Clickable 19F NMR Probes
- Description: A collection of 9 structurally diverse fluoroalkyl azides which can be used both as clickable 19F NMR probes for structural biology/advanced materials as well as a source of fluorinated functionalities for medicinal chemistry, agrochemistry or advanced materials. Suitable for high-throughput lead discovery technologies, such as combinatorial chemistry, synthesis DNA-encoded libraries and fragment-based drug discovery (FBDD).
- Composition: The kit provides a variety of 9 clickable fluoroalkyl azides that serve as 19F NMR probes or sources of fluorinated drug-like functionalities. Each of the fluoroalkyl azides is aliquoted 5 x 10 mg in plastic vials and additionally sealed in metalized pouches under inert gas.
Introduction
The unique features of fluorinated compounds, such as their near absence in living systems and favourable NMR properties (abundance, sensitivity and large span of chemical shifts) make 19F NMR spectroscopy a popular tool for in vitro monitoring of interactions of small-molecule drugs, peptides, proteins, glycans and nucleic acids and also for in-cell NMR experiments.
How do fluorinated azides fit into this picture?
Instead of conducting laborious de novo synthesis of complex biomolecules using custom-made fluorinated amino acids, nucleotides or glycans, the more easily available alkynylated biomolecules can be site-selectively and reliably clicked to a selected fluorinated azide that is well-suited for the specific sensing task. This approach significantly cuts down development costs and allows to easily test a variety of 19F NMR probes. .
With a library of clickable azides (containing magnetically equivalent fluorines) in hand, 19F NMR probe screening becomes much more straightforward and less expensive.
The fluoroalkyl azides in the kit have dual use - they can be equally used as interesting and sometimes hitherto unreported building blocks for drug discovery or to decorate alkynylated advanced materials with various fluorinated functionalities.
Nonafluoro-t-butyl ethers
Nonafluoro-t-butyl ethers are typical representatives of the relatively hydrophobic high-intensity 19F NMR probes. Depending on whether the reporting group needs to reflect changes in the chemical environment close to the attachment point or farther from it, short or medium length fluoroalkyl azide can be selected.
Derivatives of azidodifluoroacetic acid
Despite being low in 19F integration intensity, derivatives of azidodifluoroacetic acid are probably one of the least sterically demanding fluoroalkyl azides that also display excellent aqueous solubility without any cosolvents.
While sodium azidodifluoroacetate introduces a charged residue, the corresponding primary amide is mildly acidic and the hydroxamic acid is expected to act as a potentional metal binder and metalloenzyme inhibitor. All these three azides are expected to have significantly lower pKa values than their nonfluorinated counterparts.
In the context of medicinal chemistry, α,α-difluorinated carboxamides and hydroxamates are potentially attractive due to their significantly altered acidobasic behaviour.
Trifluoromethyl ketones
Due to the powerful electron-withdrawing effect of the CF3-group, trifluoromethyl ketones are excellent carbonyl electrophiles which reversibly form adducts with various nucleophiles, such as water, oxygen- and nitrogen-centered nucleophiles derived from amino acid side chains.
Therefore they can be used to sense the local degree of hydration, proximity of certain amino acids, such as serine, act as a reversible "molecular glue" or represent the warhead part of a reactive inhibitor. It has been shown that trifluoromethyl ketones inhibit serine proteases through hemiacetal-forming interference with the oxyanion hole.
Other fluorinated aromatic azides
In the context of structural 19F NMR studies, bis(trifluoromethyl)-azidomethylbenzene and 4-azidophenylbis(trifluoromethyl)carbinol represent medium intensity probes. While the sensing performance of the highly lipophilic bis(trifluoromethyl) azidomethylbenzene is based on π-π interactions, the mildly acidic fluorinated tertiary alcohol might additionally act as a hydrogen bond donor.
In medicinal chemistry, bis-trifluoromethylated aromatic scaffolds represent a privileged motif.
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