Probing of the cis-5-phenyl proline scaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureus sortase SrtA isoform.

Journal Article (Journal Article)

cis-5-Phenyl prolinates with electrophilic substituents at the fourth position of a pyrrolidine ring were synthesized by 1,3-dipolar cycloaddition of arylimino esters with divinyl sulfone and acrylonitrile. 4-Vinylsulfonyl 5-phenyl prolinates inhibit Staphylococcus aureus sortase SrtA irreversibly by modification of the enzyme Cys184 and could be used as hits for the development of antibacterials and antivirulence agents.

Full Text

Duke Authors

McCafferty, Dewey G.

Cited Authors

Kudryavtsev, KV; Bentley, ML; McCafferty, DG

Published Date

April 2009

Published In

Bioorganic & Medicinal Chemistry

Volume / Issue

17 / 7

Start / End Page

2886 - 2893

PubMed ID

19269184

Pubmed Central ID

PMC2663005

Electronic International Standard Serial Number (EISSN)

1464-3391

International Standard Serial Number (ISSN)

0968-0896

Digital Object Identifier (DOI)

10.1016/j.bmc.2009.02.008

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