Combinatorial library of low molecular-weight organo- and hydrogelators based on glycosylated amino acid derivatives by solid-phase synthesis

Shigeki Kiyonaka, Seiji Shinkai, Itaru Hamachi

Research output: Contribution to journalArticle

134 Citations (Scopus)

Abstract

A combinatorial approach for the synthesis of supramolecular gelators as new organic materials is described herein. In the course of the development of a convenient and flexible solid-phase synthesis of the artificial glycolipids, some of these compounds were accidentally found to act as low molecular-weight gelators toward organic solvents. Using this combinatorial solid-phase synthesis of glycosylated amino acetates, screening and optimization of low molecular-weight organo/hydro-gelators were efficiently carried out. We found that an N-acetyl-galactosamine-appended amino acid ester (GalNAc-aa) efficiently gelates a broad spectrum of organic solvents. More interestingly, some GalNAc-aa derivatives displayed an excellent hydrogelation capability. Transmission electron microscopy, scanning electron microscopy, confocal laser scanning microscopy, and FT-IR were used for characterization of the gel structure. It is indicated that supramolecular fibers supported by strong hydrogen-bonding networks are entangled so that the resulting spaces can immobilize a number of solvent molecules effectively. In addition, the supramolecular hydrogel consisting of GalNAc-sucglu(O-methyl-cyc-pentyl)2 is stable even under high salt concentrations probably due to its nonionic character and as a result, a native protein is successfully entrapped in the gel matrix without denaturation.

Original languageEnglish
Pages (from-to)976-983
Number of pages8
JournalChemistry - A European Journal
Volume9
Issue number4
DOIs
Publication statusPublished - Feb 17 2003

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Amino acids
Molecular weight
Derivatives
Amino Acids
Organic solvents
Galactosamine
Gels
Denaturation
Hydrogel
Glycolipids
Hydrogels
Esters
Hydrogen bonds
Microscopic examination
Screening
Acetates
Salts
Transmission electron microscopy
Proteins
Scanning

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Combinatorial library of low molecular-weight organo- and hydrogelators based on glycosylated amino acid derivatives by solid-phase synthesis. / Kiyonaka, Shigeki; Shinkai, Seiji; Hamachi, Itaru.

In: Chemistry - A European Journal, Vol. 9, No. 4, 17.02.2003, p. 976-983.

Research output: Contribution to journalArticle

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