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Related Concept Videos

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

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Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
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Nucleophilic Substitution Reactions02:34

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Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
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Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

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Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
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Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives01:15

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Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and their derivatives. In these reactions, the leaving group attached to the acyl group is substituted by a nucleophile. The general mechanism proceeds via two steps.
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Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

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Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Structural basis for NONO-specific modification by the α-chloroacetamide compound (R)-SKBG-1.

Alessia Vincenza Florio1, Corinne Buré2, Sébastien Fribourg3

  • 1INSERM U1212, CNRS UMR5320, Université de Bordeaux, 2 Rue Hoffmann Martinot, 33000 Bordeaux, France; Department of Biological, Chemical and Pharmaceutical Sciences and Technology, University of Palermo, Via Archirafi 28, Palermo, Italy.

Cell Chemical Biology
|January 10, 2026
PubMed
Summary
This summary is machine-generated.

Researchers detailed how a small molecule, (R)-SKBG-1, specifically targets the NONO protein, an RNA-binding protein implicated in cancer. This structural and binding analysis provides a foundation for developing new cancer drugs.

Keywords:
DBHSPSPC1SFPQcancerligandmass spectrometry

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Structural Biology

Background:

  • RNA-binding proteins (RBPs) play crucial roles in cellular functions and are linked to genetic diseases.
  • NONO, an RBP involved in mRNA splicing, DNA repair, and organelle stability, is a target for cancer drug development.
  • Small-molecule inhibitors targeting NONO have been identified.

Purpose of the Study:

  • To elucidate the molecular basis of NONO targeting by the α-chloroacetamide molecule (R)-SKBG-1.
  • To determine the specific binding interaction between (R)-SKBG-1 and NONO.
  • To investigate the enantiomer selectivity of this interaction.

Main Methods:

  • Mass spectrometry measurements to analyze binding.
  • Crystal structure determination of the (R)-SKBG-1-NONO homodimer complex.
  • Analysis of conformational changes upon binding.

Main Results:

  • The study determined the crystal structure of the NONO homodimer bound to (R)-SKBG-1.
  • Specific binding of (R)-SKBG-1 to NONO was confirmed.
  • Conformational plasticity of (R)-SKBG-1 upon covalent binding to NONO was revealed.

Conclusions:

  • The findings provide a detailed molecular understanding of (R)-SKBG-1 interaction with NONO.
  • This structural insight offers an experimental rationale for designing and optimizing NONO-targeting ligands.
  • The results support the potential development of (R)-SKBG-1 or its derivatives as anti-cancer therapeutics.