Tetrahydrofuran amino acids—versatile building blocks for unnatural biopolymers: lack of secondary structure in oligomeric carbopeptoids derived from a D-galacto-5-(aminomethyl) tetrahydrofuran-2-carboxylic acid

Abstract

The efficient synthesis of a D-galacto-configured tetrahydrofuran amino acid from a seven-carbon lactone as a monomer for the generation of sequence-defined structured biopolymer mimics is described. Investigations into the characteristics of homooligomeric derivatives of this monomer indicate that they do not adopt well defined secondary structures. The unanticipated formation of a heterooligomeric derivative and investigations into its solution structure are also described.