New peptidomimetics containing the Tic moiety were synthesized in enantiomerically pure form and their conformational features were studied by NMR, IR, and molecular modeling techniques. The presence of a reverse turn conformation was observed in all the structures, suggesting the key role of the scaffold as reverse turn inducer. In particular, all the analyses led to the conclusion that a β-turn conformation is mostly stabilized in tetrapeptide mimetic 4b and in hexapeptide mimetics 5a,b. In the case of 5a,b, the C1 stereochemistry plays a central role in determining stable conformations, supporting the formation of a β-hairpin arrangement with a 14-membered intramolecular hydrogen bond ring only in 5b.
Synthesis of tetrahydroisoquinoline-based pseudopeptides and their characterization as suitable reverse turn mimetics / G. Lesma, E. Meschini, T. Recca, A. Sacchetti, A. Silvani. - In: TETRAHEDRON. - ISSN 0040-4020. - 63:5(2007), pp. 5567-5578.
|Titolo:||Synthesis of tetrahydroisoquinoline-based pseudopeptides and their characterization as suitable reverse turn mimetics|
LESMA, GIORDANO (Primo)
SACCHETTI, ALESSANDRO (Penultimo)
SILVANI, ALESSANDRA (Ultimo)
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2007|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1016/j.tet.2007.04.024|
|Appare nelle tipologie:||01 - Articolo su periodico|