Synthesis of VIP-Lipopeptide Using a New Linker to Modify Liposomes

Synthesis of VIP-Lipopeptide Using a New Linker to Modify Liposomes

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 selec...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 2013-11, Vol.61 (11), p.1184
Hauptverfasser: Masaka, Toru, Matsuda, Takuya, Li, Yingpeng, Koide, Yuki, Takami, Akira, Yano, Kenji, Imai, Ryosuke, Ichihara, Risa, Yagi, Nobuhiro, Suzuki, Hideharu, Hikawa, Hidemasa, Terada, Katsuhide, Yokoyama, Yuusaku
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0009-2363
1347-5223