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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.

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Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...

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Related Experiment Video

Updated: Aug 29, 2025

Enhanced Reduced Representation Bisulfite Sequencing for Assessment of DNA Methylation at Base Pair Resolution

Enhanced Reduced Representation Bisulfite Sequencing for Assessment of DNA Methylation at Base Pair Resolution

Published on: February 24, 2015

On-DNA Reductive Amination and Alkylation.

¹Encoded Library Technologies/NCE Molecular Discovery, R&D Medicinal Science and Technology, GlaxoSmithKline, Cambridge, MA, USA. jing.5.chai@gsk.com.

Methods in Molecular Biology (Clifton, N.J.)

|September 9, 2022

Summary

This summary is machine-generated.

On-DNA reductive amination and alkylation are efficient methods for creating carbon-nitrogen bonds using diverse chemical building blocks. These reactions are crucial for DNA-encoded library (DEL) synthesis.

Keywords:

DNA-encoded library (DEL)Reductive alkylation Reductive amination

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Atomic Force Microscopy Investigations of DNA Lesion Recognition in Nucleotide Excision Repair

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Published on: May 24, 2017

Area of Science:

Organic Chemistry
Medicinal Chemistry
Chemical Biology

Background:

Carbon-nitrogen (C-N) bond formation is fundamental in synthetic chemistry.
DNA-encoded libraries (DELs) offer a powerful platform for drug discovery.
Efficient methods for modifying DNA-bound molecules are essential for DEL synthesis.

Purpose of the Study:

To highlight the utility of on-DNA reductive amination and alkylation for C-N bond formation.
To emphasize the role of these reactions in DNA-encoded library synthesis.
To showcase the versatility offered by commercially available building blocks.

Main Methods:

On-DNA reductive amination: reacting on-DNA aldehydes with amine building blocks.
On-DNA alkylation: reacting on-DNA amines with aldehyde building blocks.
Utilizing diverse, commercially available aldehyde and amine building blocks.

Main Results:

Established robust methods for C-N bond formation directly on DNA.
Demonstrated the broad applicability of these reactions using a wide array of building blocks.
Facilitated the synthesis of complex molecules within DNA-encoded libraries.

Conclusions:

On-DNA reductive amination and alkylation are highly effective strategies for DEL synthesis.
The availability of diverse building blocks significantly enhances the scope of DEL construction.
These methods provide a versatile toolkit for generating large and diverse chemical libraries for drug discovery.