title: Design and synthesis of an artificial ladder-shaped polyether that interacts with glycophorin A.
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 alpha-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 (C(alpha)-Hcdots, three dots, centeredO) with the GXXXG motif.
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan.
authors.forename: Kohei
authors.initials: K
authors.lastname: Torikai
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Yari
authors.forename: Megumi
authors.initials: M
authors.lastname: Mori
authors.forename: Satoru
authors.initials: S
authors.lastname: Ujihara
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Matsumori
authors.forename: Michio
authors.initials: M
authors.lastname: Murata
authors.forename: Tohru
authors.initials: T
authors.lastname: Oishi
mesh_terms: D002922:Ciguatoxins / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry; D006021:Glycophorins / Q000737:chemistry*; D008387:Marine Toxins / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D008978:Mollusk Venoms; D035964:Oxocins / Q000737:chemistry*; D000095702:Polyether Toxins
chemical_list: D002922:Ciguatoxins; D004987:Ethers; D004988:Ethers, Cyclic; D006021:Glycophorins; D008387:Marine Toxins; D008978:Mollusk Venoms; D035964:Oxocins; C458159:gymnocin A; C043466:brevetoxin B; D000095702:Polyether Toxins; C066632:yessotoxin