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Related Concept Videos

Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Amines to Amides: Acylation of Amines01:19

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...
What are Lipids?01:31

What are Lipids?

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Lipids are a structurally and functionally diverse group of hydrocarbons—compounds consisting of carbon and hydrogen atoms. The carbon-carbon and carbon-hydrogen bonds...
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Overview of Fatty Acid Metabolism01:28

Overview of Fatty Acid Metabolism

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Updated: Jun 28, 2026

Enrichment of Mammalian Tissues and Xenopus Oocytes with Cholesterol
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Published on: March 25, 2020

Steroids linked with amide bond-extended cholesterol.

Ivan Cerný1, Milos Budesínský, Vladimír Pouzar

  • 1Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., 166 10 Prague 6, Czech Republic. cerny@ouchb.cas.cz

Steroids
|October 28, 2008
PubMed
Summary

Researchers synthesized novel oligosteroids, linear cholesterol-like molecules, by linking cholesterol units with etienic acid derivatives. This work expands the chemical diversity of steroidal compounds for potential applications.

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High-throughput Nitrobenzoxadiazole-labeled Cholesterol Efflux Assay
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High-throughput Nitrobenzoxadiazole-labeled Cholesterol Efflux Assay
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High-throughput Nitrobenzoxadiazole-labeled Cholesterol Efflux Assay

Published on: January 7, 2019

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Supramolecular Chemistry

Background:

  • Cholesterol is a fundamental biomolecule with diverse biological roles.
  • Modifying cholesterol structures can lead to novel compounds with unique properties.
  • Oligosteroids represent a class of molecules with potential applications in materials science and medicine.

Purpose of the Study:

  • To design and synthesize a new class of linear cholesterol-like molecules.
  • To explore the formation of oligosteroids with varying numbers of cholesterol units.
  • To investigate novel synthetic strategies for constructing steroidal assemblies.

Main Methods:

  • Design of linear cholesterol-based molecules incorporating etienic acid derivatives.
  • Synthesis of oligosteroids comprising two to four cholesterol units.
  • Utilizing amide bond formation for inter-steroid linkages.
  • Adaptation of the 1-hydroxybenzotriazole active ester method for efficient coupling.
  • Employing disteroids as advanced building blocks in the synthesis.

Main Results:

  • Successful synthesis of novel oligosteroids with defined lengths (dimers, trimers, tetramers).
  • Demonstration of the efficacy of the amide bond and active ester method for steroidal conjugation.
  • Establishment of a strategy using disteroids to build larger oligosteroid structures.
  • Characterization of the synthesized oligosteroid compounds.

Conclusions:

  • A new family of linear oligosteroids has been effectively synthesized.
  • The developed synthetic methodology allows for controlled assembly of steroidal units.
  • These novel cholesterol derivatives offer a platform for further exploration in various scientific fields.