Synthesis and surface properties of monoeicosapentaenoyl trehalose

European Food Research and Technology (Impact Factor: 1.56). 07/2009; 229(3):403-408. DOI: 10.1007/s00217-009-1049-5


Eicosapentaenoyl trehalose was transesterified with eicosapentaenoic acid ethyl ester and trehalose in tert-butanol using microbial lipase. Reversed phase high-performance liquid chromatography coupled with diode array detection
and electrospray ionization mass spectrometry (RPHPLC-DAD–ESI-MS) analysis showed that the monoester and diester existed in
the reaction mixture. Silica gel column chromatography was adopted to pretreat the reactive mixture then the eluted monoeicosapentaenoyl
trehalose was further purified using semi-preparative HPLC. The structure of the compound was confirmed by ESI-MS and nuclear
magnetic resonance (NMR) as 6-O-monoeicosapentaenoyl trehalose. Subsequently, the surface properties of monoeicosapentaenoyl trehalose were investigated.
The results indicated that the surface tension, CMC, γCMC and ΔG
mico decreased with increasing temperature, however, the area occupied per molecule increased very little.

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    ABSTRACT: In this study, we report the self-assembling properties of 6-O-alkyltrehaloses with different chain lengths, that is, octyl, decyl, dodecyl, tetradecyl, and hexadecyl, under aqueous conditions. The materials were synthesized from trehalose via five reaction steps. The scanning electron microscopy (SEM), transmission electron microscopy (TEM), powder X-ray diffraction (XRD), and dynamic light scattering (DLS) measurements indicated that the self-assembling property of 6-O-dodecyltrehalose was completely different from that of the other derivatives. The former primarily formed spherical micelles in water, which further assembled into face-centered cubic-based aggregates when dried. The latter derivatives, on the other hand, formed vesicle-type particles via the formation of lamellar-like planes, which further merged with each other, most likely by the fusion of the planes, to construct larger aggregates.
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    ABSTRACT: It was shown that reaction of trehalose with one equivalent of a fatty acid in pyridine promoted by one equivalent of the uronium-based coupling agent TBTU at room temperature gives a good yield of the primary ester accompanied by small amounts of the diprimary ester, using hexanoic, palmitic, and oleic acids as examples. Reactions using two equivalents of the fatty acids gave the symmetrical diesters. The monoesters can be reacted with different fatty acids to give non-symmetric 6,6'-diesters in very good yields. Compounds synthesized include the most abundant component of the very complex maradolipid mixture, 6-O-(13-methyltetradecanoyl)-6'-O-oleoyltrehalose, and a component potentially present in this mixture, 6-O-(12-methyltetradecanoyl)-6'-O-oleoyltrehalose, a derivative of an ante fatty acid. The C5-C6 rotameric populations of 6-O-monoesters, symmetrical 6,6'-diesters, and 2,6,6'-triesters of fatty acids were calculated from the values of the H5-H6R and H5-H6S coupling constants and found to be similar to those found for glucose. The rotameric population of the monosubstituted glucose residue in the 2,6,6'-triesters was altered considerably to favor the gt rotamer, presumably because of attraction between the 2- and 6'-fatty acid chains.
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