Optimization of sucrose 1’-position modification with 3-(trifluoromethyl)diazirinyl benzylbromide derivatives for photoaffinity labeling

Abstract

Sucrose is well known as naturally occurring sweeteners. Photoreactive sucrose derivative containing 3-(trifluoromethyl)diazirinyl moiety is designed for photoaffinity labeling. As 1'-hydroxyl group of sucrose is well known to be less reactive than other primary alcohols, the optimization of reaction conditions for diazirinyl benzyl bromide derivative at sucrose 1'-postion was examined to elucidate the functional analysis of sweet receptors.

Application of Appel reaction to the primary alcohol groups of fructooligosaccharides: Synthesis of 6,6′,6′′-trihalogenated 1-kestose derivatives

“…This phenomena also occurred when sucrose was used. 12,16,17 According to these approaches, the bromination product of 1-kestose was determined to be 1'',2,3,3',3'',4,4',4''-octa-O-acetyl-6,6',6''-tribromo-6,6',6''-trideoxy-1-kestose (4).…”

Recent progress in the use of diaziridine-based sweetener derivatives to elucidate the chemoreception mechanism of the sweet taste receptor

“…at 60 °C for 24 h afforded a moderate yield (∼60%) for benzylation. 30 However, the conditions with large excess were not suitable for rare benzyl halide derivatives. A detailed analysis of the reaction mixture revealed that the benzyl alcohol derivatives were generated under the reaction conditions.…”