Sugar-induced chiral orientation of boronic-acid-appended amphiphile clusters formed in the dipalmitoylphosphatidylcholine (DPPC) membrane

Taro Kimura, Masayuki Takeuchi, Itaru Hamachi, Seiji Shinkai

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A horonic-acid-appended amphiphile bearing an azobenzene chroniophore in the chain center (3) was synthesized. Although 3 could not form the membrane-like, ordered aggregate by itself, it formed a phase-separated aggregate in a dipalmitoylphosphatidylcholine (DPPC) matrix membrane. When saccharides were added, the boronic acid group reversibly formed the saccharide complexes, and 3 in the DPPC matrix membrane became CD-active with the appearance of exciton-coupling bands. Comparison of the saccharide absolute configuration with the CD intensity established that the saccharide possessing the OH group (as 3-OH, 4-OH, and 5-CH2OH) in the same side as the cis-1,2-diol gives the strong CD band. Judging from the structure of 3-saccharide complexes, these "same-side" OH groups can enjoy intermolecular hydrogen-bonding interactions, which eventually induce the chiral orientation of azobenzene chromophores. This is a novel membrane system useful to read oui the information stored in the saccharide structure and to create novel membrane structures by added saccharides.

Original languageEnglish
Pages (from-to)379-388
Number of pages10
JournalIsrael Journal of Chemistry
Volume36
Issue number4
DOIs
Publication statusPublished - Jan 1 1996

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Boronic Acids
1,2-Dipalmitoylphosphatidylcholine
Amphiphiles
Sugars
Membranes
Bearings (structural)
Membrane structures
Chromophores
Hydrogen bonds
Acids
azobenzene

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Sugar-induced chiral orientation of boronic-acid-appended amphiphile clusters formed in the dipalmitoylphosphatidylcholine (DPPC) membrane. / Kimura, Taro; Takeuchi, Masayuki; Hamachi, Itaru; Shinkai, Seiji.

In: Israel Journal of Chemistry, Vol. 36, No. 4, 01.01.1996, p. 379-388.

Research output: Contribution to journalArticle

Kimura, Taro ; Takeuchi, Masayuki ; Hamachi, Itaru ; Shinkai, Seiji. / Sugar-induced chiral orientation of boronic-acid-appended amphiphile clusters formed in the dipalmitoylphosphatidylcholine (DPPC) membrane. In: Israel Journal of Chemistry. 1996 ; Vol. 36, No. 4. pp. 379-388.
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