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Synthesis of thiazole, imidazole and oxazole containing amino acids for peptide backbone modification
Author(s) -
Stankova Ivanka G.,
Videnov Georgi I.,
Golovinsky Evgeny V.,
Jung Guenther
Publication year - 1999
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/(sici)1099-1387(199909)5:9<392::aid-psc209>3.0.co;2-8
Subject(s) - oxazole , thiazole , chemistry , oxazoline , imidazole , combinatorial chemistry , peptide , stereochemistry , pyridine , peptidomimetic , amino acid , acetonitrile , organic chemistry , biochemistry , catalysis
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. Copyright © 1999 European Peptide Society and John Wiley & Sons, Ltd.