Design and synthesis of an artificial ladder-shaped polyether that interacts with glycophorin A

Kohei Torikai, Hiroshi Yari, Megumi Mori, Satoru Ujihara, Nobuaki Matsumori, Michio Murata, Tohru Oishi

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Ladder-shaped polyether (LSP) compounds, such as brevetoxins and ciguatoxins, are thought to interact with transmembrane (TM) proteins. As a model LSP compound, we designed and synthesized an artificial tetracyclic ether (1) and evaluated its interaction with glycophorin A (GpA), a membrane protein known to dimerize or oligomerize between membrane-integral α-helical domains. Model compound 1 was found to induce the dissociation of oligomeric GpA in a similar manner to natural LSPs when examined by SDS-PAGE. The results suggest that even an artificial tetracyclic ether possesses the ability to interact with TM proteins, presumably through the intermolecular hydrogen bonds (Cα-H ⋯ O) with the GXXXG motif.

Original languageEnglish
Pages (from-to)6355-6359
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume16
Issue number24
DOIs
Publication statusPublished - Dec 15 2006
Externally publishedYes

Fingerprint

Glycophorin
Polyethers
Ladders
Ether
Ciguatoxins
Polyacrylamide Gel Electrophoresis
Hydrogen
Hydrogen bonds
Membrane Proteins
Proteins
Membranes
brevetoxin

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Design and synthesis of an artificial ladder-shaped polyether that interacts with glycophorin A. / Torikai, Kohei; Yari, Hiroshi; Mori, Megumi; Ujihara, Satoru; Matsumori, Nobuaki; Murata, Michio; Oishi, Tohru.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 16, No. 24, 15.12.2006, p. 6355-6359.

Research output: Contribution to journalArticle

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AU - Murata, Michio

AU - Oishi, Tohru

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