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Peptidoglycan Synthesis

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Structure of PeptidoglycanPeptidoglycan is a vital structural component of the bacterial cell wall, providing mechanical strength and shape to the cell. It consists of repeating units of two sugars—N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM)—linked by β-1,4 glycosidic bonds. These sugar chains are cross-linked by short peptide chains, forming a mesh-like polymer that surrounds the bacterial plasma membrane.Cytoplasmic Phase – Precursor SynthesisPeptidoglycan...

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Related Experiment Video

Updated: Sep 21, 2025

An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity

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Published on: November 2, 2016

Synthesis of Pleuromutilin.

Nicholas J Foy¹, Sergey V Pronin¹

¹Department of Chemistry, University of California, Irvine, California 92697-2025, United States.

Journal of the American Chemical Society

|June 2, 2022

Summary

Researchers synthesized pleuromutilin, a potent bacterial protein synthesis inhibitor. This 16-step synthesis efficiently assembles the cyclooctane fragment using oxidative ring-expansion and stereocontrolled reactions.

Area of Science:

Organic Chemistry
Medicinal Chemistry
Natural Product Synthesis

Background:

Pleuromutilin is a key structural class of antibiotics that inhibit bacterial protein synthesis.
Efficient and stereocontrolled synthesis of complex natural products like pleuromutilin is crucial for drug development.
Previous synthetic routes may lack efficiency or stereochemical control.

Purpose of the Study:

To describe a novel and efficient synthetic route to the potent bacterial protein synthesis inhibitor, pleuromutilin.
To establish a strategy for the assembly of the critical cyclooctane fragment.
To achieve complete stereochemical control throughout the synthetic sequence.

Main Methods:

Utilized an oxidative ring-expansion strategy for the cyclooctane fragment assembly.

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Employed cycloaddition and radical cyclization events to rapidly establish the perhydroindanone motif.

Implemented judicious tactical choices to ensure complete stereochemical relay.

Main Results:

Successfully synthesized pleuromutilin, a potent inhibitor of bacterial protein synthesis.
The synthetic strategy enabled rapid establishment of the required perhydroindanone connectivity.
The target natural product was prepared in an efficient 16-step sequence from commercially available starting materials.

Conclusions:

The described synthetic strategy is highly effective for constructing the pleuromutilin core structure.
This approach offers a stereocontrolled and efficient pathway to a valuable class of antibiotics.
The methodology could be applicable to the synthesis of other complex natural products.