Synthesis of a C3-symmetric molecular scaffold inspired by Lissoclinum cyclopeptides for the construction of large receptors.
In: Abstracts of Papers, 229th ACS National Meeting, San Diego, CA, United States, March 13-17, 2005
Heidelberg,Germany.: Organisch-Chemisches Institut,Ruprecht-Karls-Universitat Heidelberg (2005), S. ORGN
Buchaufsatz / Kapitel / Fach: Chemie
In Lissoclinum cyclopeptide alkaloids, oxazole, thiazole, oxazoline and thiazoline moieties alternate with std. amino acid residues. These five-membered heterocyclic rings result from condensation of serine, threonine and cysteine side chains with the preceding carbonyl groups in a peptide sequence. The unique macrocyclic heterocyclic scaffolds present in Lissoclinum cyclopeptides are expected to offer great opportunities for mol. recognition. In our research work a novel C3-sym. scaffold has been efficiently synthesized. In this analog of Lissoclinum cyclopeptides the oxazole and thiazole moieties are replaced by imidazole units. The scaffold exhibits the property that variable receptor arms can be easily attached by simple alkylation reactions. The utility of the scaffold as a skeleton for large receptors has been examd. with a corresponding trisbipyridyl deriv. toward phloroglucinol.