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Organic Compounds

Organic Compounds

All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...

Prochirality

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...

IUPAC Nomenclature of Aldehydes

IUPAC Nomenclature of Aldehydes

Aldehydes are named based on the systematic nomenclature rules set by the IUPAC. For acyclic aldehydes, the longest carbon chain containing the aldehydic (–CHO) group is considered the parent chain. The aldehyde is named by replacing the last letter “e” in the hydrocarbon name with “al”. For instance, a simple, seven-carbon-membered acyclic aldehyde is called heptanal, derived from heptane. The carbon chain is numbered starting from the aldehydic carbon, although the aldehydic carbon’s locant...

Phase II Reactions: Acetylation Reactions

Phase II Reactions: Acetylation Reactions

Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...

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Related Experiment Video

Updated: Jun 4, 2026

Histone Modification Screening using Liquid Chromatography, Trapped Ion Mobility Spectrometry, and Time-Of-Flight Mass Spectrometry

Histone Modification Screening using Liquid Chromatography, Trapped Ion Mobility Spectrometry, and Time-Of-Flight Mass Spectrometry

Published on: January 12, 2024

N-propionylation.

Z Guo¹, H Jennings

¹Institute for Biological Science, National Research Council of Canada, Ottawa, ON, Canada.

Methods in Molecular Medicine

|February 22, 2011

Summary

This summary is machine-generated.

Serogroup B Neisseria meningitidis vaccines are lacking due to the poor immunogenicity of the group B meningococcal polysaccharide. Molecular mimicry with human tissues hinders effective vaccine development.

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A Strategy for Sensitive, Large Scale Quantitative Metabolomics

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Published on: May 27, 2014

Area of Science:

Immunology
Vaccinology
Microbiology

Background:

Serogroup B Neisseria meningitidis is a significant global health concern.
Current vaccines are not fully effective against this pathogen.
The group B meningococcal polysaccharide exhibits poor immunogenicity in both adults and infants.

Purpose of the Study:

To investigate the challenges in developing an effective vaccine against Serogroup B Neisseria meningitidis.
To understand the reasons behind the failure of polysaccharide-based and conjugate vaccines.

Main Methods:

Review of existing literature on meningococcal polysaccharide immunogenicity.
Analysis of the chemical structure of the group B meningococcal polysaccharide.
Exploration of molecular mimicry as a potential mechanism.

Main Results:

The group B meningococcal polysaccharide is a homopolymer of α(2-8)-linked sialic acid residues.
Conjugation technology, while successful for other polysaccharides, failed to elicit a significant immune response for the group B type.
Molecular mimicry between the bacterial polysaccharide and human tissue antigens (gangliosides, N-CAMs) is a likely cause for the poor immune response.

Conclusions:

The structural similarity between the group B meningococcal polysaccharide and human antigens poses a significant hurdle for vaccine development.
Further research is needed to overcome the immune tolerance induced by molecular mimicry for effective Serogroup B Neisseria meningitidis vaccines.