Synthesis of essramycin and comparison of its antibacterial activity.
The triazolopyrimidine natural product essramycin (1) was synthesized without the use of protecting groups via a two-step reaction scheme involving a 3-amino-1,2,4-triazole intermediate, and its structure was unequivocally determined. However, in contrast to the natural product, the synthetic essramycin (1) did not display any antibacterial activity.
Institute for Molecular Bioscience, University of Queensland, St Lucia, Queensland 4072, Australia.
Ernest H L
EH
Tee
Tomislav
T
Karoli
Soumya
S
Ramu
Johnny X
JX
Huang
Mark S
MS
Butler
Matthew A
MA
Cooper
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013302:Streptomyces / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000900:Anti-Bacterial Agents; D011744:Pyrimidinones; D014230:Triazoles; C532326:essramycin