Síntesis de gamma-aminoácidos funcionalizados con polietilenglicoles

Abstract

Cyclicpeptides formed by stereo-alternating amino acids subunits are macromolecules with the ability of adopting a planar conformation and self-stack on top of each other through the formation of hydrogen bonds to give nanotubes. The peptide nanotubes external surface can be modulated by the side chain of the amino acids used in the cyclic peptides. The incorporation of γ-amino acids in the peptide skeleton provides to the cyclic peptides new properties like the inner modulation for the synthesis of ion selective channels. This functionalizacion in contrast with other systems i.e. carbon nanotubes, is at the moment impossible to other nanotube forming strategies. Hence, the first synthetic steps towards the construction of a new nanotube based on α,γ-cyclicpeptides is the γ-amino acid synthesis. In this work, we synthesized the γ-amino acid called Acp (cis-3-aminecyclicpentanecarboxylic acid) from the Vince´s lactame and then it was modified at the amino group by a covalent coupling with a polietelenglycol group (PEG). These γ-amino acids with polietelenglycol groups could create hidrophylic channel useful to carry out molecular or ion transport in cell membranes like specific proteins.