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Investigation into the functional impact of the vancomycin C-ring aryl chloride.

ABSTRACT: A vancomycin aglycon analogue that possesses a reduced C-ring and an intact E-ring chloride was prepared and its antimicrobial activity towards Staphylococcus aureus and binding affinity to model cell wall ligands were established. Comparison of the derivative with a series of vancomycin aglycon analogues that possess and lack the chloro substituents on the aryl C- and E-rings defines the impact and further refines the role the C-ring chloride plays in promoting both target binding affinity and binding selectivity for d-Ala-d-Ala and its impact on antimicrobial activity.

SUBMITTER: Pinchman JR

PROVIDER: S-EPMC3757926 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Investigation into the functional impact of the vancomycin C-ring aryl chloride.

Pinchman Joseph R JR Boger Dale L DL

Bioorganic & medicinal chemistry letters 20130704 17

A vancomycin aglycon analogue that possesses a reduced C-ring and an intact E-ring chloride was prepared and its antimicrobial activity towards Staphylococcus aureus and binding affinity to model cell wall ligands were established. Comparison of the derivative with a series of vancomycin aglycon analogues that possess and lack the chloro substituents on the aryl C- and E-rings defines the impact and further refines the role the C-ring chloride plays in promoting both target binding affinity and ...[more]

PMID: 23880541

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