Design, synthesis and stimuli responsive gelation of novel stigmasterol-amino acid conjugates

0365267 - ÚEB 2012 RIV US eng J - Journal Article
Svobodová, Hana - Nonappa, J. - Wimmer, Zdeněk - Kolehmainen, E.
Design, synthesis and stimuli responsive gelation of novel stigmasterol-amino acid conjugates.
Journal of Colloid and Interface Science. Roč. 361, č. 2 (2011), s. 587-593. ISSN 0021-9797. E-ISSN 1095-7103
R&D Projects: GA MŠMT 2B06024; GA MŠMT(CZ) OC10001
Institutional research plan: CEZ:AV0Z50380511
Keywords : Stigmasterol * Amino acid * LMOG
Subject RIV: CC - Organic Chemistry
Impact factor: 3.070, year: 2011

An efficient synthesis of three novel stigmasterol-amino acid (glycine, L-leucine and L-phenylalanine) conjugates as stimuli responsive gelators is reported. The gelation properties of the prepared compounds were investigated in a variety of organic as well as aqueous solvents. The most striking finding of our investigation was that the hydrochloride salts of the prepared conjugates acted as gelators, whereas the neutral conjugates were either non-gelators or formed only a weak gel in anisole. The hydrochloride salts of stigmasteryl glycinate and L-Ieucinate form gels in n-alcohols (n = 4-10) and in ethane-1,2-diol, and that of stigmasteryl L-phenylalaninate forms gels in aromatic solvents and in tetrachloromethane. These unique properties of the gelators were explored to prepare stimuli responsive, "acid-base" triggered reversible sol-gel transitions. The gelators and their gels were characterized by liquid and solid-state NMR as well as FT-IR.
Permanent Link: http://hdl.handle.net/11104/0200550