Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules. Issue 70 (13th August 2018)

• Record Type: Journal Article
• Authors: Sumii, Yuji; Hibino, Hayata; Saidalimu, Ibrayim; Kawahara, Hidehisa; Shibata, Norio
• Is Part Of: Chemical communications. Volume 54:Issue 70(2018)
• Page Start: 9749
• Page End: 9752
• Publication Date: 2018-08-13
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc05588b
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Galactose-conjugated fluorinated and non-fluorinated proline oligomers were synthesized and evaluated as antifreeze molecules. 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.