Sugar‐Induced Chiral Orientation of Boronic‐Acid‐Appended Amphiphile Clusters Formed in the Dipalmitoylphosphatidylcholine (DPPC) Membrane

A boronic‐acid‐appended amphiphile bearing an azobenzene chromophore 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‐CH 2 OH) 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 out the information stored in the saccharide structure and to create novel membrane structures by added saccharides.