Expedient synthesis of pseudo-Pro-containing peptides: towards constrained peptidomimetics and foldamers.
The reaction of sulfonyl peptides containing L- or D-configured Ser or Thr with bis(succinimidyl) carbonate in the presence of a catalytic amount of a base affords, in solution or in the solid phase, the corresponding peptides with one or two, consecutive or alternate oxazolidin-2-ones (Oxd). The Oxd ring can be regarded to as a pseudo-Pro with an exclusively trans conformation of the preceding peptide bond; homochiral Oxd-containing peptides adopt extended conformations, while the presence of a D-configured Oxd favours folded conformations.
Department of Chemistry G. Ciamician, University of Bologna, via Selmi 2, 40126 Bologna, Italy.
Rossella
R
De Marco
Alessandra
A
Tolomelli
Marilena
M
Campitiello
Pasqualina
P
Rubini
Luca
L
Gentilucci
D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*; D057786:Peptidomimetics / Q000138:chemical synthesis*; D011392:Proline / Q000737:chemistry
D010455:Peptides; D057786:Peptidomimetics; D011392:Proline