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

• Masaka Toru

  School of Pharmaceutical Sciences, Toho University Sakura Medical Center, Toho University

• Matsuda Takuya

  School of Pharmaceutical Sciences, Toho University

• Li Yingpeng

  School of Pharmaceutical Sciences, Toho University

• Koide Yuki

  School of Pharmaceutical Sciences, Toho University

• Takami Akira

  School of Pharmaceutical Sciences, Toho University

• Yano Kenji

  School of Pharmaceutical Sciences, Toho University

• Imai Ryosuke

  School of Pharmaceutical Sciences, Toho University

• Ichihara Risa

  School of Pharmaceutical Sciences, Toho University

• Yagi Nobuhiro

  School of Pharmaceutical Sciences, Toho University

• Suzuki Hideharu

  School of Pharmaceutical Sciences, Toho University

• Hikawa Hidemasa

  School of Pharmaceutical Sciences, Toho University

• Terada Katsuhide

  School of Pharmaceutical Sciences, Toho University

• Yokoyama Yuusaku

  School of Pharmaceutical Sciences, Toho University

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.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 61 (11), 1184-1187, 2013

  The Pharmaceutical Society of Japan

Keywords

• drug delivery system
• linker
• isopropylidene-D-threitol
• lipopeptide
• peptide synthesizer

Details

• CRID: 1390001204177923968
• NII Article ID: 130003360912
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c13-00518
• COI: 1:STN:280:DC%2BC3sbisFyitw%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 024957254
• PubMed: 23979293
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I024957254
• Web Site: https://www.jstage.jst.go.jp/article/cpb/61/11/61_c13-00518/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2014184038
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• Abstract License Flag: Disallowed