Enantioselective synthesis of new conformationally constrained sugar-like gamma-, delta-, epsilion-amino acids, delta-peptides and nucleoside amino acids

摘要

The new conformationally constrained sugar-like gamma-, delta-, and epsilon-amino acids were synthesized in enantiomerically pure in an efficient manner from trans-2,3-disubstituted gamma-butyrolactone These novel amino acids can serve as useful templates to induce interesting secondary structures in peptides. Furthermore, the novel delta-peptide was synthesized from conformationally constrained Boc-delta-amino acid via an iterative peptide coupling strategy. Finally, a new strategy was developed leading to the nucleoside amino acid starting from the amine (5-Allyl-4-[(4-methoxy-benzylamino)-methyl]-dihydro-furan. The introduction of pyrimidine base onto the lactone followed by oxidation of the allyl double bond as key steps. This novel nucleoside amino acid can serve as useful building block towards PNA analogue synthesis.