Synthesis of bridged sugar amino acids: a new entry into conformationally locked δ- and ε-amino acids

The synthesis of three methylene bridged sugar amino acids is described. Key transformations in the synthetic strategy are a CO-insertion on fully protected ribose, an aldol condensation with formaldehyde and an oxetane forming cyclisation step. A novel Leu-enkephalin analogue containing the δ-SAA was prepared using standard solution phase peptide chemistry.