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Related Experiment Video

Updated: Apr 18, 2026

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028

Published on: January 13, 2017

Solid-phase total synthesis of daptomycin and analogs.

Chuda Raj Lohani¹, Robert Taylor, Michael Palmer

¹Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario, Canada , N2L 3G1.

Organic Letters

|January 31, 2015

Summary

Solid-phase synthesis of the antibiotic daptomycin was achieved. A novel analog lacking specific amino acids showed potent antimicrobial activity comparable to the original drug.

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Last Updated: Apr 18, 2026

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028

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Production and Testing of Antimicrobial Peptides and Their Mimics

Production and Testing of Antimicrobial Peptides and Their Mimics

Published on: April 10, 2026

Area of Science:

Medicinal Chemistry
Organic Synthesis
Microbiology

Background:

Daptomycin is a clinically important cyclic lipodepsipeptide antibiotic.
Its complex structure presents synthetic challenges.
Novel analogs are needed to overcome resistance and improve efficacy.

Purpose of the Study:

To develop a robust solid-phase synthesis for daptomycin.
To create and evaluate daptomycin analogs with modified structures.
To identify analogs with potent antimicrobial activity.

Main Methods:

Employed a solid-phase synthesis strategy.
Utilized a combination of alpha-azido and Fmoc-protected amino acids.
Synthesized several daptomycin analogs, including those lacking kynurenine and (2S,3R)-methylglutamate.

Main Results:

Successfully achieved an entirely solid-phase synthesis of daptomycin.
Synthesized daptomycin analogs with structural modifications.
One analog, devoid of kynurenine and (2S,3R)-methylglutamate, demonstrated a Minimum Inhibitory Concentration (MIC) close to that of daptomycin.

Conclusions:

Solid-phase synthesis is a viable approach for daptomycin and its analogs.
Structural modifications can yield analogs with potent antimicrobial activity.
This synthetic strategy facilitates the exploration of daptomycin's structure-activity relationship.