A series of Nα-protected, monodispersed homo-oligopeptide esters to the octamer level from L-Cα-methyl, C α-n-propylglycine [or Cα-methylnorvaline, (αMe)Nva] has been synthesized by solution methods and fully characterized. The preferred conformation of these homo-oligomers in solution has been assessed by FT-IR absorption and 1H NMR techniques. Moreover, the molecular structures of the homotrimer and homotetramer have been determined in the crystal state by X-ray diffraction. The obtained results strongly support the view that right-handed, single or multiple, and consecutive β bends are preferentially adopted by the conformationally restricted L-(αMe)Nva homo-oligomers. In particular, 310 helices are formed by the longest homo-oligomers. It is our contention that the [(αMe)Nva]n peptides represent the best available choice among Cα-trasubstituted α-amino acid-based homo-oligomers for the construction of relatively easy to make, rigid foldamers with a well-defined screw-sense bias.

Cα-Methyl, Cα-n-Propylglycine Homo-oligomers / Formaggio F.; Crisma M.; Toniolo C.; Broxterman Q.B.; Kaptein B.; Corbier C.; Saviano M.; Palladino P.; Benedetti E.. - In: MACROMOLECULES. - ISSN 0024-9297. - ELETTRONICO. - 36:(2003), pp. 8164-8170. [10.1021/ma030327v]

Cα-Methyl, Cα-n-Propylglycine Homo-oligomers

Palladino P.;
2003

Abstract

A series of Nα-protected, monodispersed homo-oligopeptide esters to the octamer level from L-Cα-methyl, C α-n-propylglycine [or Cα-methylnorvaline, (αMe)Nva] has been synthesized by solution methods and fully characterized. The preferred conformation of these homo-oligomers in solution has been assessed by FT-IR absorption and 1H NMR techniques. Moreover, the molecular structures of the homotrimer and homotetramer have been determined in the crystal state by X-ray diffraction. The obtained results strongly support the view that right-handed, single or multiple, and consecutive β bends are preferentially adopted by the conformationally restricted L-(αMe)Nva homo-oligomers. In particular, 310 helices are formed by the longest homo-oligomers. It is our contention that the [(αMe)Nva]n peptides represent the best available choice among Cα-trasubstituted α-amino acid-based homo-oligomers for the construction of relatively easy to make, rigid foldamers with a well-defined screw-sense bias.
36
8164
8170
Formaggio F.; Crisma M.; Toniolo C.; Broxterman Q.B.; Kaptein B.; Corbier C.; Saviano M.; Palladino P.; Benedetti E.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/1256386
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