Synthesis of VIP-Lipopeptide using a New Linker to Modify Liposomes: Towards the Development of a Drug Delivery System for Active Targeting

Abstract

A new component for the solid phase peptide synthesis of lipopeptide, 2-[(4R,5R) -5-({[(9H-fluoren-9-yl)methoxy]-carbonylaminomethyl}-2,2-dimethyl-1,3-dioxolan-4-yl) methoxy]acetic acid (2), was designed and synthesized from (-)-2,3-O-isopropylidene-d-threitol (3) in 4 steps. The key step was the selective alkylation of 3 with benzyl bromoacetate in the presence of Cs₂CO₃. Vasoactive intestinal peptide (VIP)-lipopeptide (1) incorporating this linker was synthesized by solid phase peptide synthesis.