213820-59-8Relevant articles and documents
Solid-phase syntheses of peptoids using Fmoc-protected N-substituted glycines: The synthesis of (retro)peptoids of leu-enkephalin and substance P
Kruijtzer, John A.W.,Hofmeyer, Lovina J.F.,Heerma, Wigger,Versluis, Cornelis,Liskamp, Rob M.J.
, p. 1570 - 1580 (1998)
A particularly interesting class of oligomeric peptidomimetics is formed by the peptoids, which consist of N-substituted glycine residues. A solid- phase synthesis method for peptoids is presented in which these residues are introduced using their Fmoc derivatives. This 'monomer' method allowed the monitored synthesis of relatively large quantities of pure peptoids as well as the translation of, in principle, any peptide into the corresponding peptoid. The required Fmoc-substituted glycines were accessible by convenient synthesis, and a number of monomers including those containing side chains with functional groups have been synthesized. The use of Fmoc monomers also allowed implementation of a solid-phase synthesis protocol on a commercial peptide synthesizer. The method was exempli- fled by the solid-phase syntheses of the (retro)peptoids of Leu-enkephalin and substance P. Mass spectrometric studies of (retro)peptoids were essential for their characterization, and the presence of the B- and Y'- type ions allows sequence analysis. Substance P (retro)peptoids were biologically active. HPLC analysis showed an increased hydrophobicity, and pepsin treatment resulted in greatly reduced degradation compared with the corresponding peptide.
