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Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules

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Abstract

Galactose-conjugated fluorinated and non-fluorinated proline oligomers that exhibit an α-helical structure with hydrophilic and lipophilic parts were designed as potential antifreeze molecules. These galactose-proline oligomers were synthesized and their physical properties were evaluated. Interestingly, the non-fluorinated galactose-proline oligomers showed in contrast to the fluorinated analogues weak antifreeze activity. The difference in antifreeze activity should be attributed to the fluorine gauche effect, which should induce a conformation in fluorinated prolines that is different from that of natural proline. The results obtained in this study thus suggest that the 3D conformation of the galactose-conjugated fluorinated and non-fluorinated proline oligomers is very important for their anti-freezing properties.

Graphical abstract: Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules

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Publication details

The article was received on 11 Jul 2018, accepted on 01 Aug 2018 and first published on 01 Aug 2018


Article type: Communication
DOI: 10.1039/C8CC05588B
Citation: Chem. Commun., 2018, Advance Article
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    Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules

    Y. Sumii, H. Hibino, I. Saidalimu, H. Kawahara and N. Shibata, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC05588B

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