Cyclic beta-peptoids.
The first synthesis of functionalized beta-peptoid macrocycles is reported. X-ray crystallographic structure of tetramer 9 reveals a C2-symmetrical derivative with unexpected all-cis-amide bonds and spatial disposition of the appendages toward the two opposite faces of the ring. Quantum calculations suggest that 9 is locked in this layout. These macrocycles constitute novel promising templates for multimeric ligation of biologically active ligands. The concept was exemplified by chemical decoration of tetramer 9 via "click" reactions.
Roy
Olivier
O
Laboratoire de Synthèse et Etude de Systèmes d'Intérêt Biologique, SEESIB (UMR 6504 - CNRS), Université Blaise Pascal - Clermont-Ferrand II, 24 avenue des Landais, 63177 Aubière Cedex, France.
Faure
Sophie
S
Thery
Vincent
V
Didierjean
Claude
C
Taillefumier
Claude
C
D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D034444:Peptoids / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D013237:Stereoisomerism
D010456:Peptides, Cyclic; D034444:Peptoids