Investigation into fiber formation in N-alkyl urea peptoid oligomers and the synthesis of a water-soluble PEG/N-alkyl urea peptoid oligomer conjugate

Abstract

The synthesis and self assembly of an N-alkyl urea peptoid oligomer/polymer conjugate that self-assembles into ribbon-like structures is reported. The aggregation of the N-alkyl urea peptoid oligomers has been investigated using NMR spectroscopy, with long and highly uniform fibers with micron dimensions observed in scanning electron microscopy images from both organo-soluble and water-soluble versions. The results of these studies indicate that hydrogen bonding likely is the major driving force for the self assembly. The oligomer was conjugated to poly(ethylene glycol) (PEG) producing a water soluble polymer/N-alkyl urea peptoid conjugate where the self-assembly of the N-alkyl urea peptoid was retained. These polymer conjugates represent a new approach to polymer biomimetic conjugates.