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Design and synthesis of new hydroxyethylamines as inhibitors of D-alanyl-D-lactate ligase (VanA) and D-alanyl-D-alanine ligase (DdlB).

Abstract：

:The Van enzymes are ATP-dependant ligases responsible for resistance to vancomycin in Staphylococcus aureus and Enteroccoccus species. The de novo molecular design programme SPROUT was used in conjunction with the X-ray crystal structure of Enterococcus faeciumd-alanyl-d-lactate ligase (VanA) to design new putative inhibitors based on a hydroxyethylamine template. The two best ranked structures were selected and efficient syntheses developed. The inhibitory activities of these molecules were determined on E. faecium VanA, and due to structural similarity and a common reaction mechanism, also on d-Ala-d-Ala ligase (DdlB) from Escherichia coli. The phosphate group attached to the hydroxyl moiety of the hydroxyethylamine isostere within these systems is essential for their inhibitory activity against both VanA and DdlB.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Sova M,Cadez G,Turk S,Majce V,Polanc S,Batson S,Lloyd AJ,Roper DI,Fishwick CW,Gobec S

doi

10.1016/j.bmcl.2009.01.034

subject

Has Abstract

pub_date

2009-03-01 00:00:00

pages

1376-9

issue

5

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(09)00069-9

journal_volume

19

pub_type

杂志文章

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