Structure and semisynthesis of platensimide A, produced by Streptomyces platensis.
Platensimycin and platencin are novel natural product antibiotics that inhibit bacterial growth by inhibiting condensing enzymes FabF and FabF/FabH of fatty acid biosynthesis pathways, respectively. Continued search for the natural congeners of these compounds led to the isolation of platensic acid, the free C-17 tetracyclic enoic acid, and platensimide A, a 2,4-diaminobutyric acid amide derivative. Isolation, structure, semisynthesis, and activity of these compounds are described.
Herath
Kithsiri B
KB
Merck Research Laboratories, Rahway, NJ 07065, USA.
Zhang
Chaowei
C
Jayasuriya
Hiranthi
H
Ondeyka
John G
JG
Zink
Deborah L
DL
Burgess
Bruce
B
Wang
Jun
J
Singh
Sheo B
SB
D000218:Adamantane / Q000737:chemistry* / Q000494:pharmacology; D062365:Aminobenzoates / Q000737:chemistry* / Q000494:pharmacology; D000613:Aminobutyrates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000627:Aminophenols / Q000737:chemistry* / Q000378:metabolism; D000813:Anilides / Q000737:chemistry* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects / Q000378:metabolism; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry* / Q000378:metabolism; D013302:Streptomyces / Q000254:growth & development / Q000378:metabolism*
D062365:Aminobenzoates; D000613:Aminobutyrates; D000627:Aminophenols; D000813:Anilides; D000900:Anti-Bacterial Agents; D001952:Bridged-Ring Compounds; D011083:Polycyclic Compounds; C530506:platensimide A; D000218:Adamantane; C510909:platensimycin; C520340:platencin