Structural studies on sweet taste inhibitors: methyl-4,6-dichloro-4,6-dideoxygalactopyranoside

Mathlouthi, Mohamed; Maciejewski, C.; Serghat, S.; Hooft, Rob; Kanters, J. A.; Kroon, Jan

doi:10.1016/0022-2860(93)85042-s

Cited by 8 publications

(3 citation statements)

References 22 publications

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“…It is also well-known that sweet and bitter tastes interact. For example, inhibition of sweet taste by inhibitors like lactisol or methyl-4,6-dichloro-4,6-dideoxygalactopyranoside was attributed to their bitterness (3). Bitterness may be suppressed by sweeteners, such as sucrose (4).…”

Section: Introductionmentioning

confidence: 99%

Hydration Properties and the Role of Water in Taste Modalities of Sucrose, Caffeine, and Sucrose−Caffeine Mixtures

Aroulmoji

Hutteau

Mathlouthi

et al. 2001

J. Agric. Food Chem.

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Solution properties of sapid molecules are informative on their type of hydration (hydrophobic or hydrophilic) and on the extent of the hydration layer. Physicochemical properties (intrinsic viscosity and apparent specific volume) and nuclear magnetic resonance (NMR) relaxation rates R(1) and R(2) for pure sucrose, bitter molecule caffeine, and their mixture were found to be relevant in the interpretation of the effects of these solutes on water mobility. Likewise, surface tension, contact angles with a hydrophobic surface, and the adhesion forces to this type of surface of the aqueous solutions of sapid molecules were found to discriminate between their effects on water cohesion and also between their taste qualities. The interpretation of the two sets of independent experimental results, namely physicochemical and spectroscopic data, helps in the elucidation of the role of water in sweet and bitter taste chemoreception.

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Section: Introductionmentioning

confidence: 99%

Hydration Properties and the Role of Water in Taste Modalities of Sucrose, Caffeine, and Sucrose−Caffeine Mixtures

Aroulmoji

Hutteau

Mathlouthi

et al. 2001

J. Agric. Food Chem.

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“…5) [10]. Introduction of 2,3-di-O-(L-alanyl) groups into the antagonist did not alter the conformations of 6-O-methyl and 6-chloro derivatives, suggesting that the stereospecificities of the hydrophobic components are similar in both the antagonist and the agonist.…”

Section: Transformation Of Sweetness Inhibitors Into Sweetenersmentioning

confidence: 91%

Design and synthesis of new sweeteners

Machinami

Fujimoto

Takatsuka

et al. 2002

Pure and Applied Chemistry

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Sweet taste induction by alkyl 2,3-di-O-(L-aminoacyloxy)-α-D-glucopyranosides requires a combination of hydrophobic α-alkoxy and hydrophilic vicinal, diequatorially oriented, L-aminoacyloxy units. Pyranoside chair conformations afford the preferred stereochemical arrangements of these residues for optimum interaction with the receptor. For the design of new sweeteners based on sweetness inhibitors,

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“…It is known that sweet and bitter tastes interact very closely with each other and both are apparently mediated by G-protein-coupled receptors. For example, inhibition of sweet taste by inhibitors like lactisol or methyl-dichlorogalactoside originates from their bitterness [2]. The change in taste modalities (sweet, sweetbitter or bitter) for chlorinated sucrose may be explained by the physicochemical properties of their aqueous mixtures [3].…”

Section: Introductionmentioning

confidence: 99%

Physico-Chemical Properties of Nicotine and Nicotine-Bitterness Inhibitor Mixtures in Aqueous Solution and the Role of Water in their Taste

Aroulmoji¹,

Mathlouthi²,

Portmann-Richardson³

2021

International Journal of Advanced Science and Engineering

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Structural studies on sweet taste inhibitors: methyl-4,6-dichloro-4,6-dideoxygalactopyranoside

Cited by 8 publications

References 22 publications

Hydration Properties and the Role of Water in Taste Modalities of Sucrose, Caffeine, and Sucrose−Caffeine Mixtures

Hydration Properties and the Role of Water in Taste Modalities of Sucrose, Caffeine, and Sucrose−Caffeine Mixtures

Design and synthesis of new sweeteners

Physico-Chemical Properties of Nicotine and Nicotine-Bitterness Inhibitor Mixtures in Aqueous Solution and the Role of Water in their Taste

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