Isolation, structure and biological activities of platensimycin B4 from Streptomyces platensis.
Platensimycin and platencin are inhibitors of FabF and FabF/H bacterial fatty acid synthesis enzymes, respectively. Discovery of natural congeners provides one of the ways to understand the relationship of chemical structure and biological function. Efforts to discover the natural analogs of platensimycin by chemical screening led to the isolation of platensimycin B(4), a glucoside congener of platensimycin. This analog showed significantly attenuated activity and critically defined the limited binding space around the aromatic ring and established the importance of the free phenolic and carboxyl group for the activity.
Zhang
Chaowei
C
Merck Research Laboratories, Rahway, NJ 07065, USA.
Ondeyka
John
J
Guan
Ziqiang
Z
Dietrich
Lisa
L
Burgess
Bruce
B
Wang
Jun
J
Singh
Sheo B
SB
D000218:Adamantane / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D062365:Aminobenzoates / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000813:Anilides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001426:Bacterial Proteins / Q000037:antagonists & inhibitors; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D005227:Fatty Acids / Q000096:biosynthesis; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D013211:Staphylococcus aureus / Q000187:drug effects / Q000201:enzymology; D013302:Streptomyces / Q000737:chemistry*; D013329:Structure-Activity Relationship
D062365:Aminobenzoates; D000813:Anilides; D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D005227:Fatty Acids; D000218:Adamantane; C510909:platensimycin