Physical properties and packing states of molecular assemblies of synthetic glycolipids in aqueous dispersions

Shinji Takeoka, Keitaro Sou, Christoph Boettcher, Jürgen Hinrich Fuhrhop, Eishun Tsuchida*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)


Amidic glycolipids, 1,5-bis-O-alkyl-N-maltooligonoyl-L-glutamate (1), having various lengths of two hydrocarbon chains (carbon number, m: 14, 16, 18) and maltooligotose with (glucose unit, n: 3, 5, 7) and a N-glycosidic lipid, 1,5-bis-O-octadecyl-N-maltopentaonosyl-L-glutamate (2) have been synthesized. The assembling structures were analyzed by microscopic observation, such as negatively stained TEM, cryo-TEM, and AFM. The glycolipid 1a (m,n: 14,5) showed a fiber-like structure in all the observed temperatures, while 1b (16,5) showed a fiber-like structure when the hydrating temperature was above the gel-to-liquid crystalline phase transition temperature (Tc ; 45°C) and a large disk-like structure when incubated below the Tc. The glycolipid 1c (18,5) took a large disk-like structure after hydration of the powder above the Tc. The glycolipids 1d (18,3) and 1e (18,7) showed a mixture of large disks and large vesicles and a mixture of small disks and micelles, respectively. The N-glycosidic lipid, 2, with no amide linkage made a vesicular structure only. The preparation procedure using high shear stress, such as extrusion and sonication, converted the large disk of 1c to smaller assemblies, such as small disk-, cone-, and granule-like assemblies, depending on the preparation conditions. The glycolipid molecules in the planer part of the disk were packed so tightly that molecular mobility was very low even above the Tc (58°C), and the reactivity of the saccharide chain against Concanavalin A was also very low, indicating that the high reactivity probably comes from the loose packing of saccharide chains around the edge part of the assemblies.

Original languageEnglish
Pages (from-to)2151-2158
Number of pages8
JournalJournal of the Chemical Society - Faraday Transactions
Issue number15
Publication statusPublished - 1998 Aug 7

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry


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