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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
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α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
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Palladium-Protein Oxidative Addition Complexes by Amine-Selective Acylation.

Heemal H Dhanjee1, Ivan Buslov1, Ian W Windsor1

  • 1Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society
|December 15, 2020
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This study introduces a novel method to create palladium oxidative addition complexes (OACs) directly on proteins using amino groups. This technique enables efficient protein-protein cross-coupling with stable, biologically active reagents.

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Area of Science:

  • Bioconjugation Chemistry
  • Organometallic Chemistry
  • Protein Engineering

Background:

  • Traditional palladium oxidative addition complexes (OACs) require aryl halide substrates and palladium(0) sources.
  • Existing methods often involve complex procedures or modifications to the protein.

Purpose of the Study:

  • To develop a new, direct strategy for synthesizing stable palladium oxidative addition complexes (OACs) on native proteins.
  • To enable efficient and selective protein-protein cross-coupling using these novel reagents.

Main Methods:

  • Utilized an amine-selective acylation reaction to transfer a palladium(II)-aryl group onto protein amino groups.
  • Developed a method for subsequent conjugation of the modified protein with a cysteine-containing protein.
  • Performed reactions in an aqueous environment under open-air conditions.

Main Results:

  • Successfully prepared stable palladium-protein OACs from native proteins, including enzymes and antibodies.
  • Demonstrated that the resulting Pd-protein OACs retain biological activity.
  • Achieved protein-protein cross-coupling at nanomolar concentrations within hours.

Conclusions:

  • Presented a simple, versatile method for creating protein-based palladium oxidative addition complexes (OACs).
  • The developed Pd-protein OACs are stable, storable, and effective for bioconjugation.
  • This approach offers a new avenue for protein modification and cross-coupling applications.