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Synthesis of thiazole, imidazole and oxazole containing amino acids for peptide backbone modification

✍ Scribed by Ivanka G. Stankova; Georgi I. Videnov; Evgeny V. Golovinsky; Guenther Jung

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 94 KB
Volume: 5
Category: Article
ISSN: 1075-2617
DOI: 10.1002/(sici)1099-1387(199909)5:9<392::aid-psc209>3.0.co;2-8

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✦ Synopsis

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.

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