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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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 strong interaction...
Covalently Linked Protein Regulators02:04

Covalently Linked Protein Regulators

Proteins can undergo many types of post-translational modifications, often in response to changes in their environment. These modifications play an important role in the function and stability of these proteins. Covalently linked molecules include functional groups, such as methyl, acetyl, and phosphate groups, and also small proteins, such as ubiquitin. There are around 200 different types of covalent regulators that have been identified.
These groups modify specific amino acids in a protein.
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
RNA Editing02:23

RNA Editing

RNA editing is a post-transcriptional modification where a precursor mRNA (pre-mRNA) nucleotide sequence is changed by base insertion, deletion, or modification. The extent of RNA editing varies from a few hundred bases, in mitochondrial DNA of trypanosomes, to a just single base, in nuclear genes of mammals. Even a single base change in the pre-mRNA can convert a codon for one amino acid into the codon for another amino acid or a stop codon. This type of re-coding can significantly affect the...

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Related Experiment Video

Updated: Jun 26, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
07:11

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Photoredox-Catalyzed Lysine C(sp3)-H Functionalization for Peptide Editing.

Christopher W Lamartina1, Paramjit S Arora1

  • 1Department of Chemistry, New York University, New York, New York 10003, United States.

Journal of the American Chemical Society
|June 24, 2026
PubMed
Summary

Researchers developed a new photoredox-catalyzed method for selective C-H functionalization of lysine residues in peptides. This technique enables diverse peptide modifications and the creation of novel peptide architectures using readily available protecting groups.

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Specificity Analysis of Protein Lysine Methyltransferases Using SPOT Peptide Arrays
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Specificity Analysis of Protein Lysine Methyltransferases Using SPOT Peptide Arrays

Published on: November 29, 2014

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Last Updated: Jun 26, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
07:11

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
11:09

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

Specificity Analysis of Protein Lysine Methyltransferases Using SPOT Peptide Arrays
08:48

Specificity Analysis of Protein Lysine Methyltransferases Using SPOT Peptide Arrays

Published on: November 29, 2014

Area of Science:

  • Organic Chemistry
  • Peptide Chemistry
  • Synthetic Chemistry

Background:

  • Selective modification of lysine residues in peptides is challenging due to side-chain flexibility and inert C-H bonds.
  • Existing methods often lack site-selectivity or require harsh conditions.

Purpose of the Study:

  • To develop a novel method for site-selective C(sp3)-H functionalization of lysine and other primary amine residues.
  • To enable late-stage diversification of peptides and access to unnatural amino acid motifs.

Main Methods:

  • Utilized photoredox catalysis to generate α-amino radical intermediates from trifluoroacetamide protecting groups.
  • Applied the method to standard Fmoc-solid phase peptide synthesis and on-resin modification.

Main Results:

  • Achieved site-selective C(sp3)-H functionalization under mild conditions.
  • Demonstrated broad substrate scope, including tolerance to various amino acid residues and alkene coupling partners.
  • Successfully performed intermolecular alkylation and intramolecular macrocyclization.

Conclusions:

  • Established redox-active amide protecting groups as versatile tools for radical generation in complex molecular settings.
  • Expanded the synthetic toolbox for late-stage peptide diversification and the construction of complex peptide architectures.