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Structural features of vancomycin

R R Pfeiffer

    Reviews of Infectious Diseases
    |November 1, 1981
    PubMed
    Summary
    This summary is machine-generated.

    Recent analytical methods fully elucidated vancomycin's structure, revealing its peptide chain, three rings, and attached disaccharide. This detailed understanding explains its mechanism of action against bacterial cell walls.

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    Area of Science:

    • Biochemistry
    • Structural Biology
    • Microbiology

    Background:

    • Vancomycin's precise molecular structure was previously incompletely understood, known only through fragmented descriptions.
    • Advances in analytical techniques were necessary to characterize the intact vancomycin molecule.

    Purpose of the Study:

    • To provide a comprehensive description of the vancomycin molecule's structure.
    • To elucidate the structural basis for vancomycin's antibiotic activity.

    Main Methods:

    • Utilized advanced analytical methods to determine the complete molecular structure.
    • Analyzed the molecular components, including the peptide chain, ring formations, and disaccharide.

    Main Results:

    • The molecular weight of vancomycin is 1,448.

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  • The structure comprises a seven-membered peptide chain with three phenylglycine units, two chlorinated tyrosines, aspartic acid, and N-methylleucine, forming three large rings via ether and carbon-carbon bonds.
  • A disaccharide (glucose and vancosamine) is attached but not part of the cyclic structure.

    • Conclusions:

    • The detailed structure of vancomycin, including its functional groups, explains its hydrogen bonding interactions with bacterial cell-wall precursors (D-alanyl-D-alanine).
    • This molecular interaction provides a basis for vancomycin's cell-wall targeting mechanism of action.
    • Vancomycin's various ionic groups influence its behavior in solutions of differing pH and composition.