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Related Concept Videos

Phase II Conjugation Reactions: Overview01:14

Phase II Conjugation Reactions: Overview

Conjugation, a key component of phase II biotransformation reactions, is a vital process in drug detoxification. It involves transferring endogenous substances like glucuronic acid, sulfate, and glycine to drugs or their metabolites formed in phase I reactions. These conjugation reactions, often catalyzed by specific enzymes, transform potentially harmful metabolites into inactive, water-soluble forms easily excreted in urine or bile. By enhancing polarity and eliminating pharmacological...
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)01:27

Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)

α,β-Unsaturated carbonyl compounds with two electrophilic sites, the carbonyl carbon, and the β carbon, are susceptible to nucleophilic attack via two modes: conjugate or 1,4-addition and direct or 1,2-addition.
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are formed faster owing to...
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds01:09

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

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.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Transfer RNA Synthesis02:36

Transfer RNA Synthesis

One of the unique features of tRNA is the presence of modified bases. In some tRNAs, modified bases account for nearly 20% of the total bases in the molecule. Altogether, these unusual bases protect the tRNA from enzymatic degradation by RNases.
Each of these chemical modifications is carried by a specific enzyme, post-transcription. All of these enzymes have unique base and site-specificity. Methylation, the most common chemical modification, is carried by at least nine different enzymes, with...
Types of RNA01:20

Types of RNA

Three main types of RNA are involved in protein synthesis: messenger RNA (mRNA), transfer RNA (tRNA), and ribosomal RNA (rRNA). These RNAs perform diverse functions and can be broadly classified as protein-coding or non-coding RNA. Non-coding RNAs play important roles in regulating gene expression in response to developmental and environmental changes. Non-coding RNAs in prokaryotes can be manipulated to develop more effective antibacterial drugs for human or animal use.
RNA Performs Diverse...

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Efficient and Site-specific Antibody Labeling by Strain-promoted Azide-alkyne Cycloaddition
09:06

Efficient and Site-specific Antibody Labeling by Strain-promoted Azide-alkyne Cycloaddition

Published on: December 23, 2016

Fast RNA conjugations on solid phase by strain-promoted cycloadditions.

Ishwar Singh1, Colin Freeman, Annemieke Madder

  • 1Department of Chemistry, NUI Maynooth, Maynooth, Republic of Ireland. ishwar.singh@strath.ac.uk

Organic & Biomolecular Chemistry
|July 4, 2012
PubMed
Summary
This summary is machine-generated.

Strain-promoted cycloaddition enables efficient RNA conjugation on solid supports. This method utilizes click chemistry with nitrile oxide dipoles, offering a faster and more reactive alternative to azides for bioconjugation.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Bioconjugation Chemistry

Background:

  • RNA conjugation is crucial for various applications, including diagnostics and therapeutics.
  • Existing methods often require harsh conditions or metal catalysts, limiting their utility.
  • Developing efficient and mild conjugation strategies is essential for advancing RNA-based technologies.

Purpose of the Study:

  • To establish strain-promoted cycloaddition as a versatile tool for solid-phase RNA conjugation.
  • To compare the reactivity of different click chemistry partners for RNA modification.
  • To demonstrate the compatibility of the method with common RNA protecting groups.

Main Methods:

  • Preparation of RNA-cyclooctyne conjugates via strain-promoted azide-alkyne cycloaddition (SPAAC) and strain-promoted nitrile oxide-alkyne cycloaddition (SPNOAC).
  • Assessment of conjugation efficiency and kinetics under various conditions.
  • Evaluation of compatibility with 2'-OMe and 2'-O-TBDMS protecting groups.
  • Testing the reactivity of diverse dipoles, including pyrenyl, coumarin, and dabcyl derivatives.

Main Results:

  • Strain-promoted cycloaddition provides an efficient method for solid-phase RNA conjugation.
  • Strain-promoted nitrile oxide-alkyne cycloaddition (SPNOAC) demonstrates higher reactivity compared to strain-promoted azide-alkyne cycloaddition (SPAAC).
  • Conjugation occurs rapidly (within 10 minutes) in aqueous solvents at room temperature, without metal catalysts.
  • The method tolerates various protecting groups and a wide range of dipole structures.

Conclusions:

  • Strain-promoted cycloaddition, particularly SPNOAC, is a powerful and rapid technique for RNA conjugation on solid supports.
  • The mild and efficient nature of this method makes it suitable for preparing diverse RNA conjugates for various applications.
  • This approach offers a significant advancement in bioconjugation strategies for nucleic acids.