Synthesis and bioactivity of thiazole and oxazole-containing peptidomimetics

Bi-Huang Hu, University of Rhode Island

Abstract

The thiazole and oxazole-containing peptides from natural sources have many important biological activities such as antitumor, antifungal, antibiotic and antiviral activities. The thiazole and/or oxazole ring systems in those biologically active peptides may be important pharmacophores and play a critical role in their activities. In chapter one, three N-protected thiazole and/or oxazole-containing amino acids were synthesized in solution in order to test this hypothesis. In chapter two, two libraries of thiazole and/or oxazole-containing peptidomimetics, and a microcin B1713-23 fragment 39 were synthesized on a solid phase. The tetrapeptide amides in the first library was synthesized on a methylbenzhydrylamine (MBHA) resin using commercially available N-Boc-L-(3)-(4-thiazolyl) alanine and N-Boc-D-(3)-(4-thiazolyl) alanine as the building blocks. The second library was synthesized on a trityl resin using 2-Fmoc-aminomethyl-thiazole-4-carboxylic acid (1), 2-Fmoc-aminomethyl-oxazole-4-carboxylic acid ( 2), and 2-(2-Fmoc-aminomethyl-oxazole-4-yl)-thiazole-4-carboxylic acid (3), which were synthesized and reported in chapter one, plus Fmoc-glycine as the building blocks. The compounds in library one showed some DNA binding activity, and compounds L2-6 and L2-9 in library two and microcin B17 fragment 39 had some inhibition activity on the growth of marine bacterium Vibrio anguillarum . ^

Subject Area

Chemistry, Organic|Chemistry, Pharmaceutical

Recommended Citation

Bi-Huang Hu, "Synthesis and bioactivity of thiazole and oxazole-containing peptidomimetics" (1999). Dissertations and Master's Theses (Campus Access). Paper AAI9945204.
http://digitalcommons.uri.edu/dissertations/AAI9945204

Share

COinS