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The structural basis for induction of VanB resistance
Steven D Dong1, Markus Oberthür, Heather C Losey
1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
Journal of the American Chemical Society
|August 1, 2002
Summary
Glycopeptide antibiotics like vancomycin and teicoplanin are crucial for treating bacterial infections. Researchers found that the core structure (aglycon) of these antibiotics, not the sugar part, triggers resistance, offering insights into overcoming it.
Area of Science:
- Microbiology
- Medicinal Chemistry
- Antibiotic Resistance
Background:
- Glycopeptide antibiotics, including vancomycin and teicoplanin, are vital last-resort treatments for bacterial infections.
- Emerging resistance in enterococci and streptococci to these drugs is a significant clinical concern.
- Vancomycin, unlike teicoplanin, induces resistance gene expression despite structural similarities.
Purpose of the Study:
- To investigate which structural components of vancomycin and teicoplanin are responsible for inducing VanB resistance.
- To elucidate the mechanism by which teicoplanin may circumvent resistance compared to vancomycin.
Main Methods:
- Synthesis of vancomycin and teicoplanin analogues using chemical and enzymatic techniques.
- Comparative analysis of structural elements (aglycon, carbohydrate) for their role in resistance induction.
- Evaluation of lipid-containing analogues to understand resistance circumvention.
Main Results:
- The aglycon (core structure) of both vancomycin and teicoplanin was identified as the key determinant for inducing VanB resistance.
- Teicoplanin and its lipid-containing analogues appear to bypass resistance mechanisms.
- The lipid chain in teicoplanin alters the antibiotic's distribution, potentially changing the blocked biosynthetic step.
Conclusions:
- The aglycon moiety of glycopeptide antibiotics is critical for triggering resistance.
- Lipid modification of vancomycin-like molecules may offer a strategy to overcome existing resistance.
- Understanding these structural-resistance relationships is essential for developing new antibiotics against resistant bacteria.
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