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.
“…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).…”
1-kestose (O-β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside) is a potential short chain fructooligosaccharide with an inulin-type skeleton. Halogenation of 1-kestose was conducted via the Appel reaction with the use of carbon tetrahalide (CBr4 or CCl4) and triphenylphosphine, which was then followed by conventional acetylation. The per-O-acetylated form of 6,6',6''-trihalogenated derivatives of 1kestose were conveniently isolated. Further deprotection of the per-O-acetylated form resulted in 6-, 6'-, and 6''-trihalogenated derivatives. The structure elucidation by one-and two-dimensional nuclear magnetic resonance established that halogenations are specific at the 6-, 6'-, and 6''-position of 1-kestose primary alcohols.
“…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).…”
1-kestose (O-β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside) is a potential short chain fructooligosaccharide with an inulin-type skeleton. Halogenation of 1-kestose was conducted via the Appel reaction with the use of carbon tetrahalide (CBr4 or CCl4) and triphenylphosphine, which was then followed by conventional acetylation. The per-O-acetylated form of 6,6',6''-trihalogenated derivatives of 1kestose were conveniently isolated. Further deprotection of the per-O-acetylated form resulted in 6-, 6'-, and 6''-trihalogenated derivatives. The structure elucidation by one-and two-dimensional nuclear magnetic resonance established that halogenations are specific at the 6-, 6'-, and 6''-position of 1-kestose primary alcohols.
“…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.…”
Section: Photoaffinity Probes For Sweetener Derivativesmentioning
The review summarized recent progress for the elucidation of the chemoreception mechanism of sweet taste receptor–sweetener interactions with photoaffinity labeling.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.