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Updated: Jun 15, 2025

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

Total Synthesis of Pedopeptin C.

Michael J Lambrecht¹, Ying Lu², Mary Kate Alexander³

¹Discovery Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.

Organic Letters

|June 13, 2025

Summary

Pedopeptins show promise against drug-resistant bacteria. This study optimized the synthesis of pedopeptin C, a challenging antibiotic, and confirmed its antibacterial activity.

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Last Updated: Jun 15, 2025

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Area of Science:

Antibiotic discovery and development
Synthetic organic chemistry
Microbiology

Background:

Pedopeptins are a class of antibiotics with activity against multidrug-resistant bacteria.
They show potential against strains resistant to last-resort antibiotics like polymyxins.
The complex structure of pedopeptins, including (E)-2-aminobut-2-enoic acid ((E)-ΔAbu), presents significant synthetic challenges.

Purpose of the Study:

To develop an optimized synthesis for pedopeptin C, a key member of the pedopeptin class.
To evaluate the antibacterial activity of the synthesized pedopeptin C.
To address the synthetic difficulties associated with pedopeptin structures.

Main Methods:

Optimization of synthetic routes for pedopeptin C.
Characterization of the synthesized compound.
In vitro testing of antibacterial activity against relevant bacterial strains.

Main Results:

An optimized synthetic strategy for pedopeptin C was successfully developed.
The synthesized pedopeptin C demonstrated antibacterial activity.
The synthesis overcomes key challenges related to the dehydroamino acid moiety.

Conclusions:

The optimized synthesis provides a viable route to pedopeptin C.
Pedopeptin C is a promising antibiotic candidate for combating resistant bacterial infections.
Further research into pedopeptins could lead to new therapeutic options.