Solid-phase synthesis of 1,3-azole-based peptides and peptidomimetics.
[reaction: see text] We report highly efficient two-step procedures for the synthesis of 1,3-oxazole-, thiazole-, and imidazole-containing peptides on solid phase from dipeptides composed of C-terminal threonine, serine, cysteine, or diaminopropionic acid by using different cyclodehydration procedures followed or preceded by oxidation. The methods are compatible with Fmoc solid-phase peptide synthesis conditions and with N-Fmoc, N-Boc, N-Cbz, and N-Alloc protecting groups.
Biron
Eric
E
Department Chemie, Lehrstuhl II für Organische Chemie, Technische Universität München, Garching, Germany.
Chatterjee
Jayanta
J
Kessler
Horst
H
D000596:Amino Acids / Q000737:chemistry*; D001393:Azoles / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D018716:Molecular Mimicry; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012694:Serine / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013912:Threonine / Q000737:chemistry
D000596:Amino Acids; D001393:Azoles; D007093:Imidazoles; D010080:Oxazoles; D010455:Peptides; D013844:Thiazoles; D013912:Threonine; D012694:Serine