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

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• 作者：Kohei Torikai ; Hiroshi Yari ; Megumi Mori ; Satoru Ujihara ; Nobuaki Matsumori ; Michio Murata ; Tohru Oishi
• 关键词：Ladder-shaped polyether ; Artificial ladder-shaped polyether ; Transmembrane protein ; Glycophorin A ; GXXXG motif
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2006
• 出版时间：15 December 2006
• 年：2006
• 卷：16
• 期：24
• 页码：6355-6359
• 全文大小：640 K

文摘

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 (C_α–H O) with the GXXXG motif.