Total Synthesis of the Post-translationally Modified Polyazole Peptide Antibiotic Goadsporin.
The structurally unique polyazole antibiotic goadsporin contains six heteroaromatic oxazole and thiazole rings integrated into a linear array of amino acids that also contains two dehydroalanine residues. An efficient total synthesis of goadsporin is reported in which the key steps are the use of rhodium(II)-catalyzed reactions of diazocarbonyl compounds to generate the four oxazole rings, which demonstrates the power of rhodium carbene chemistry in organic chemical synthesis.
School of Chemistry, University Park, Nottingham, NG7 2RD, UK.
Hannah L
HL
Dexter
School of Chemistry, University Park, Nottingham, NG7 2RD, UK.
Huw E L
HE
Williams
School of Chemistry, University Park, Nottingham, NG7 2RD, UK.
William
W
Lewis
School of Chemistry, University Park, Nottingham, NG7 2RD, UK.
Christopher J
0000-0003-0487-041X
CJ
Moody
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D036341:Intercellular Signaling Peptides and Proteins; D008968:Molecular Conformation; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011499:Protein Processing, Post-Translational; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D036341:Intercellular Signaling Peptides and Proteins; D010455:Peptides; C449027:goadsporin
antibiotics; diazo compounds; heterocycles; peptides; total synthesis