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Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Electrophilic Aromatic Substitution: Nitration of Benzene

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Alcohols from Carbonyl Compounds: Reduction

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Boron-Assisted Selective Citrulline Modification under Mild Conditions.

Hailong Zhao¹, Aidong Shan², Yunshi Liang¹

¹Artemisinin Research Center and The First Affiliated Hospital, Guangzhou University of Chinese Medicine, Guangzhou 510405, China.

Organic Letters

|August 23, 2022

Summary

Researchers developed a new biocompatible method for studying protein citrullination under neutral conditions. This technique allows for selective and irreversible modification of citrulline residues, overcoming limitations of previous acidic methods.

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Area of Science:

Biochemistry
Proteomics
Chemical Biology

Background:

Protein citrullination is a crucial post-translational modification.
Existing methods require harsh acidic conditions (pH <1), limiting physiological studies.
Understanding citrullination is vital for various biological processes and diseases.

Purpose of the Study:

To develop a biocompatible and efficient method for studying protein citrullination.
To enable the selective modification of citrulline residues under physiological conditions.
To provide a novel tool for investigating protein citrullination in biological systems.

Main Methods:

Development of an *o*-boron-assisted chemical modification strategy.
Application of the method under neutral pH conditions.
Demonstration of selective and irreversible modification of citrulline residues.

Main Results:

A novel, biocompatible method for protein citrullination was successfully established.
The *o*-boron-assisted method operates effectively under neutral conditions.
The modification of citrulline residues was shown to be selective and largely irreversible.

Conclusions:

The developed *o*-boron-assisted method offers a significant advancement for studying protein citrullination.
This technique overcomes the limitations of harsh acidic conditions, enabling research under physiological relevance.
It presents a valuable new tool for the broader scientific community exploring protein citrullination.