Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.8K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.8K
Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

5.5K
Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
5.5K
Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

6.7K
Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
6.7K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

3.2K
The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
3.2K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

7.2K
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.
7.2K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.8K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
4.8K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

On-DNA Epoxide Synthesis and Ring-Opening Derivatization.

Organic letters·2026
Same author

Efficacy and hepatotoxicity of Psoralea corylifolia L.: A meta-analysis and machine learning assessment in postmenopausal osteoporosis.

Journal of ethnopharmacology·2026
Same author

Kaempferol inhibits oxidative stress-induced ferroptosis via the ROS/P38MAPK pathway to delay intervertebral disc degeneration: a combinatorial study of cell, animal, and transcriptomic evidence.

International immunopharmacology·2026
Same author

Adaptation and Validation of the Social Media Cyberbullying Victimization Scale Among Chinese College Students: Cross-Sectional Study.

Journal of medical Internet research·2026
Same author

Senescence-associated secretory phenotype: the "pathogenic" factor driving orthopedic degenerative diseases and its regulation.

Frontiers in aging·2026
Same author

The Mediating Role of Interpersonal Needs in Perceived Parenting Styles and Social Media Addiction Among University Students: Cross-Sectional Study.

Journal of medical Internet research·2026
Same journal

Photoinduced Alkene Carbothiolation via Fe/Ni Dual Catalysis.

Organic letters·2026
Same journal

Synthesis of Azo-Substituted Benzoxazin-4-ones by Base-Mediated Addition of Diazenyl Anions to Isatoic Anhydrides.

Organic letters·2026
Same journal

Dual-Pathway Skeletal Editing of Isoquinolines.

Organic letters·2026
Same journal

Visible-Light-Induced Radical C-N Coupling for Access to Hydrazine Derivatives.

Organic letters·2026
Same journal

Olefination of Alcohols and Alkyl Halides via Oxidative Alkyl Electrophile-Olefin Metathesis.

Organic letters·2026
Same journal

Regioselective Hydroarylation of Ynamides: A Direct Synthetic Route to Trisubstituted Enamides.

Organic letters·2026
See all related articles
  1. Home
  3. Accessing Α-ketoamides On Dna Through A Coupling-oxidation Strategy.
  1. Home
  3. Accessing Α-ketoamides On Dna Through A Coupling-oxidation Strategy.

Related Experiment Video

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

25.7K

Accessing α-Ketoamides on DNA through a Coupling-Oxidation Strategy.

Xianfu Fang1,2, Xin Wang2, Qigui Nie2,3

  • 1Pharmaceutical Department, Chongqing University Three Gorges Hospital, Chongqing University, Chongqing 404100, China.

Organic Letters
|January 14, 2026

View abstract on PubMed

Summary
This summary is machine-generated.

Researchers developed a novel on-DNA synthesis strategy to create α-ketoamides, crucial for drug discovery. This method expands DNA-encoded libraries (DELs) by enabling efficient synthesis of diverse α-ketoamide compounds.

More Related Videos

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.7K
Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes
07:44

Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes

Published on: July 6, 2016

11.6K

Related Experiment Videos

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

25.7K
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.7K
Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes
07:44

Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes

Published on: July 6, 2016

11.6K

Area of Science:

  • Medicinal Chemistry
  • Synthetic Chemistry
  • Biotechnology

Background:

  • α-Ketoamides are vital pharmacophores in drug discovery.
  • Their incorporation into DNA-encoded libraries (DELs) is limited by a lack of efficient on-DNA synthetic methods.

Purpose of the Study:

  • To develop a robust on-DNA synthetic strategy for α-ketoamide precursors.
  • To expand the chemical diversity accessible within DNA-encoded libraries.

Main Methods:

  • An on-DNA coupling-oxidation strategy was employed to synthesize DNA-conjugated α-hydroxyamides.
  • Subsequent oxidation converted α-hydroxyamides into α-ketoamides.

Main Results:

  • The protocol demonstrated broad substrate scope and excellent functional group tolerance, especially for mandelic acid derivatives.
  • It enabled the collective transformation of α-hydroxyamide libraries into α-ketoamide libraries.
  • This significantly increased the chemical space accessible for DELs.

    • Conclusions:

    • A novel and efficient on-DNA synthetic route to α-ketoamides has been established.
    • This method overcomes previous limitations, enabling broader application of DELs in drug discovery.
    • The strategy facilitates the generation of diverse α-ketoamide libraries for screening.