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Convergent Synthesis of Repeating Peptides (Val-X-Leu-Pro-Pro-Pro) 8 Adopting a Polyproline II Conformation

1996; American Chemical Society; Volume: 61; Issue: 20 Linguagem: Inglês

10.1021/jo960987g

1520-6904

Ionara I. Dalcol, Miquel Pons, M. Dolors Ludevid, Ernest Giralt,

Antimicrobial Peptides and Activities

The N-terminal domain of maize gamma-zein has a repetitive structure (Val-His-Leu-Pro-Pro-Pro)(8) that has recently been shown to adopt an amphipathic polyproline II type conformation in aqueous solution. We report here the synthesis and conformational analysis of three model peptides (Val-X-Leu-Pro-Pro-Pro)(8) (X = Ala (1), Glu (2), Lys (3)). The three compounds have been synthesized in a very efficient way using a convergent solid-phase strategy. Circular dichroism shows unequivocally that the three model peptides adopt polyproline II (PPII) type conformations under a variety of experimental conditions and that neither the presence of histidine nor amphipathicity of the peptide is an absolute requirement for adopting the native conformation. These results open the door for the de novo design of compounds with PPII conformations and must be taken into account in the structure prediction of protein structures from sequence data banks.