Hetaryleneaminopolyols and hetarylenecarbopeptoids:: a new type of glyco- and peptidomimetics.: Syntheses and studies on solution conformation and dynamics

Ready access to a new class of oligomers has been demonstrated by the synthesis of hetarylene-aminopolyols and hetarylenecarbopeptoids using 3-hydroxymethyl-5-(4-amino-4-deoxy-D-arabinotetritol-1-yl)-2-methylfuran and 5-(4-amino-4-deoxy-D-arabinotetritol-1-yl)-2-methyl-3-furoic acid as novel scaffolds. The conformational behavior of peptidomimetics 22, 23, 25, 26, and 36 have been analyzed by NMR spectroscopy and extensive molecular dynamics simulations. MD simulations using the GB/SA continuum solvent model for water and the MM3* force field provide a population distribution of conformers which satisfactorily agrees with the experimental NMR data for the torsional degrees of freedom of the molecule.