Structure elucidation of Sch 538415, a novel acyl carrier protein synthase inhibitor from a microorganism

Min Chu; Ronald Mierzwa; Ling Xu; Shu-Wei Yang; Ling He; Mahesh Patel; Jill Stafford; David Macinga; Todd Black; Tze-Ming Chan; Vincent Gullo

doi:10.1016/j.bmcl.2003.07.011

Structure elucidation of Sch 538415, a novel acyl carrier protein synthase inhibitor from a microorganism

Bioorg Med Chem Lett. 2003 Nov 3;13(21):3827-9. doi: 10.1016/j.bmcl.2003.07.011.

Authors

Min Chu¹, Ronald Mierzwa, Ling Xu, Shu-Wei Yang, Ling He, Mahesh Patel, Jill Stafford, David Macinga, Todd Black, Tze-Ming Chan, Vincent Gullo

Affiliation

¹ Schering-Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, USA. [email protected]

PMID: 14552789
DOI: 10.1016/j.bmcl.2003.07.011

Abstract

A novel acyl carrier protein synthase inhibitor, Sch 538415 (1), was isolated from an unidentified bacterial microbe. Structure elucidation of 1 was accomplished based on analysis of spectroscopic data including UV, MS and 2D-NMR spectra. Compound 1 exhibited inhibitory activity in the acyl carrier protein synthase (AcpS) assay with an IC(50) value of 4.19 microM and showed antibacterial activity against Staphylococcus aureus in the agar diffusion assay.

MeSH terms

Aza Compounds / chemical synthesis*
Aza Compounds / chemistry
Aza Compounds / isolation & purification
Bacteria / chemistry
Chromatography, Liquid
Fermentation
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Weight
Protein Synthesis Inhibitors / chemistry
Protein Synthesis Inhibitors / isolation & purification
Protein Synthesis Inhibitors / pharmacology*
Quinones / chemical synthesis*
Quinones / chemistry
Quinones / isolation & purification
Staphylococcus aureus / drug effects
Structure-Activity Relationship
Transferases (Other Substituted Phosphate Groups) / antagonists & inhibitors*

Substances

Aza Compounds
Protein Synthesis Inhibitors
Quinones
Sch 538415
Transferases (Other Substituted Phosphate Groups)
holo-(acyl-carrier-protein) synthase