b3-Heptadepsipeptides with the hydroxybutanoic acid unit at various positions in the peptidic sequence were synthesized in soln. using Boc-protection and/or Z-protection. DCC/DMAP or EDC/DMAP coupling conditions were used for the ester bond formation and EDC/HOBt for the amide bonds. Structural investigations by CD and NMR spectroscopy point to the importance of the contribution of hydrogen bonds on the stability of the 314-helix over that of the b-amino acid residue's backbone. [on SciFinder (R)]
Mahajan, Y. R., Senthilkumar, R., Rueping, M., & Seebach, D. (2002). b-depsipeptides: synthesis and structural studies. Peptides 2002, Proceedings of the European Peptide Symposium, 27th, Sorrento, Italy, Aug.31-Sept.6, 2002. Laboratorium fuer Organische Chemie der Eidgenoessischen Technischen Hochschule Zuerich,ETH-Hoenggerberg,Zurich,Switz.