title: Synthesis of trifunctional thiazolyl amino acids and their use for the solid-phase synthesis of small molecule compounds and cyclic peptidomimetics.
abstract: Chiral thiazolyl amino acid building blocks for the solid-phase synthesis of small molecules, peptides, and cyclic peptides have been designed and synthesized starting from Fmoc protected asparagine and glutamine. In efforts to demonstrate the usefulness and validity of such building blocks, a small library of 16 new thiazole containing small molecules has been prepared and characterized. Additionally, we report the use of the newly prepared trifunctional thiazolyl glutamine for the on-resin, head-to-tail synthesis of cyclic peptides.
authors.affiliation: Torrey Pines Institute for Molecular Studies , 11350 Southwest Village Parkway, Port St. Lucie, Florida 34986, United States.
authors.forename: Heather A
authors.initials: HA
authors.lastname: Michaels
authors.forename: Diana C
authors.initials: DC
authors.lastname: Velosa
authors.forename: Adel
authors.initials: A
authors.lastname: Nefzi
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D057786:Peptidomimetics; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000596:Amino Acids; D010456:Peptides, Cyclic; D057786:Peptidomimetics; D054852:Small Molecule Libraries; D013844:Thiazoles