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Vancomycin
Glycopeptide antibiotic
Cynthia Tallent
Introduction
Glycopeptide antibiotic
 Used to treat gram-positive bacteria
 Inhibits bacterial cell wall production
 Resistant strains have been identified

Outline
History
 Properties
 Inhibition of Cell Wall Biosynthesis
 Resistance
 Analog Research
 Review

History
Discovered in 1956
 Originally from Indonesian soil
cultures
 Structure was elucidated in 1983

Structure
Properties
Administered Intravenously
 Administered Orally
 pH 3-5 in aqueous solution
 P = 2.5

Bacterial Cell Walls
Composed of peptidoglycans
 Help to prevent lysis
 Gram positive bacteria have thick cell
walls

Cell Wall Biosynthesis
Inhibition of Cell Wall
Biosynthesis
Vancomycin Resistance
Enterococcus and Staphylococcus
aureus
 Changes D-Ala-D-Ala to D-Ala-DLactate
 Bifunctional model
 Add Hydrophobic substituents to
vancosamine sugar

Christopher Walsh

Adding Hydrophobic substituents to
vancosamine sugar

Loss of affinity did not lose antibacterial effect

Disaccharide fragments are effective
Analogs
DCB-PV is
effective against
Vancomycin
Resistant Strains
Review