Chemical & Pharmaceutical Bulletin 2013-01-01

Synthesis of VIP-lipopeptide using a new linker to modify liposomes: towards the development of a drug delivery system for active targeting.

Toru Masaka, Takuya Matsuda, Yingpeng Li, Yuki Koide, Akira Takami, Kenji Yano, Ryosuke Imai, Risa Ichihara, Nobuhiro Yagi, Hideharu Suzuki, Hidemasa Hikawa, Katsuhide Terada, Yuusaku Yokoyama

Index: Chem. Pharm. Bull. 61(11) , 1184-7, (2013)

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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.