Exploration of the site-specific nature and generalizability of a trimethylammonium salt modification on vancomycin: A-ring derivatives
- Resource Type
- Authors
- Dale L. Boger; Zhi-Chen Wu
- Source
- Tetrahedron
- Subject
- chemistry.chemical_classification
Membrane permeabilization
010405 organic chemistry
Chemistry
Organic Chemistry
Salt (chemistry)
biochemical phenomena, metabolism, and nutrition
010402 general chemistry
Antimicrobial
01 natural sciences
Biochemistry
Combinatorial chemistry
Article
Bacterial cell structure
0104 chemical sciences
Drug Discovery
medicine
Vancomycin
medicine.drug
- Language
- ISSN
- 0040-4020
Vancomycin analogues bearing an A-ring trimethylammonium salt modification were synthesized and their antimicrobial activity against vancomycin-resistant Enterococci (VRE) was evaluated. The modification increased antimicrobial potency and provided the capability to induce bacteria cell membrane permeabilization, but both properties were weaker than that found with our earlier reported similar C-terminus modification. The results provide further insights on the additive effect and generalizability of the structural and site-specific nature of a peripheral quaternary trimethylammonium salt modification of vancomycin.