Synthesis of thiazole, imidazole and oxazole containing amino acids for peptide backbone modification.
Novel 5-ring heterocyclic building blocks are synthesized. These can be incorporated into analogs of peptide antibiotics such as microcin B17, which is a potent DNA-gyrase inhibitor that exhibits eight thiazole and oxazole moieties. In particular, the syntheses of imidazole and bisoxazole amino acids as novel peptidomimetics are reported, this includes a new procedure for the oxidative conversion of the intermediates oxazoline, imidazoline as well as oxazole-oxazoline into the corresponding heteroaromatic compounds. A mixture of 1,8-diazabicyclo-[5.4.0.]-undec-7-ene carbon tetrachloride/acetonitrile and pyridine proved to be a very effective and mild agent.
Stankova
I G
IG
Department of Chemistry, Southwest University N. Rilski, Blagoevgrad, Bulgaria. IVANKAST@aix.swu.bg
Videnov
G I
GI
Golovinsky
E V
EV
Jung
G
G
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000737:chemistry; D001430:Bacteriocins / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis*; D018716:Molecular Mimicry; D010080:Oxazoles / Q000138:chemical synthesis*; D010455:Peptides / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis*
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D001430:Bacteriocins; D007093:Imidazoles; D010080:Oxazoles; D010455:Peptides; D013844:Thiazoles; C020411:microcin; C029899:imidazole