Synthesis and Study of Short Chain α, β-Hybrid Peptides as Biologically Active Molecules

Abstract

In order to increase the oral bioavailability without compromising biological potency or specificity of peptide drugs, α-β hybrid bioactive peptides analogues of Casmorphins present in bovine milk were synthesized. α-β hybrid peptides are stable in aqueous solution and are resistant towards proteolytic cleavage. α-Gly-β-Pro, α-Phe-β-Pro, β-Pro-α-Tyr and α-Gly-β-Pro-β-Pro-β-Tyr were synthesized using LPS. Functional groups were protected using Boc and O-Bn group. α-amino acids were converted to β-amino acids using Arndt-Eistert method followed by Wolff rearrangement. Coupling of α and β, β and β amino acids were carried out using EDC and HOBt. Synthesized α-β hybrid peptides were characterized using FTIR, NMR and CHNS.