Nutrasweet

The sensation of sweetness obviously involves interaction between the sweetener and some sort of biological receptor. It might be expected, therefore, that sweeteners share common structural features. Is this the case  

Examine the structures oisucrose, the natural sweetener, and saccharin, sodium cyclamate and aspartame (Nutrasweet), three of the most common artificial sweeteners. What, if any, structural features do these molecules have in common Compare electrostatic potential maps for the different sweeteners. Are there any significant features in common Based on yom findings, do you think it is likely that entirely different artifical sweeteners might be discovered Explain. 

One similarity which sweeteners need to possess is water solubility. Point out structural features in both natural and artificial sweeteners which are likely to make them soluble. 

Aspartame is a dipeptide, made up of aspartic acid and phenylalanine. Identify all the chiral atoms in aspartame and assign R/S stereochemistry to each. Is the stereochemistry the same as in the natural forms of aspartic acid andphenylalaninel 

Electrostatic potential map for aspartame shows negatively-charged regions (in red) and positively-chai ged regions (in blue). 

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NutraSweet Nutricote Nutrient removal Nutrients Nutrients, trace Nutation... 

Meiji Seika Kaisha (Japan) Beghin Say (France) Coors Biotech (U.S.) NutraSweet (U.S.)... 

F.4 What is the mass percentage composition of aspartame, CI4H 8N205, an artificial sweetener sold as NutraSweet ... 

C13-0115. The artificial sweetener aspartame (NutraSweet) is Ihe methyl ester of Ihe following dipeptide ... 

Nutraceuticals, 12 61 17 643-683 efficacy of, 17 647-649 future trends in, 17 674 health benefits of, 17 645-649 identification of, 17 646-647 market for, 17 673-674 product classes of, 17 649-673 safety of, 17 647 vitamins as, 17 649-655 NutraSweet, 24 226, 229 Nutrient feeding, for fermentation, 11 39 Nutrient Management Plans, 11 126-127 Nutrient Profiles (AAFCO), 10 857, 858-859t Nutrients... 

Aspartame, a dipeptide (aspartic acid + phenylalanine) artificial sweetener marketed under the trade name Nutrasweet... 

Aspartame, N-a-L-aspartyl-L-phenylalanine methyl ester, trade names NutraSweet , and Aspartil , is a dipeptide derivative. Like dipeptides aspartame is metabolised into the constituents, i.e. amino acids and methanol. Therefore studies into the metabolic behaviour and the fate of metabolites were carried out. Levels of blood aspartate and glutamate were measured after intake of high aspartame doses. Changes were transient and allegations of influences of high aspartame levels on brain function could never be verified. 

Center for Applied Catalysis, Seton Hall University, South Orange, NJ 07079 The NutraSweet Corporation, Chicago, IL 60654... 

It is enantioselective and forms the peptide bond only with L-Phe-OMe and not with D-Phe-OMe. This enables the use of cheaper racemic precursor (also because D-Phe-OMe can be racemised, see Figure 4.8), whereas the competing chemical synthesis process of Nutrasweet has to use more expensive L-Phe-OMe. 

The profit potential of aspartame was a major factor in the takeover of Searle by Monsanto. (Current aspartame sales are ca. 10 ton/a, equivalent to ca. 850 x lO /a). The success of the Nutrasweet Co. in establishing aspartame in the market. This has... 

The expiry of Nutrasweet patents, first in Europe, then in the USA, has opened up the... 

Regulatory approval for aspartame produced by Nutrasweet was very long and expensive, although this was no longer such a big problem for Holland Sweetener Co. 

In the future aspartame can expect to encounter competition from new high intensity sweeteners such as sucralose which is produced by Tate Lyle/Johnson Johnson and alitame (Pfizer), which have advantages such as even higher sweetness and, in the case of sucralose, heat stability. In response Nutrasweet are busy developing a new very high intensity sweetener (Sweetener 2000), which is reputed to be 10,000 times as sweet as sucrose. 

Demand for L-phenylalanine was exclnsively from the Monsanto-Ajinomoto joint-venture Nutrasweet Company (the first manufacturer of aspartame). 

Aspartame. Aspartame [22839-47-0] [53906-69-1] (APM, L-aspartyl-L-phenylalanine methyl ester) (1), also known under the trade names of NutraSweet and EQUAL, is the most widely used nonnutritive sweetener worldwide. This dipeptide ester was synthesized as an intermediate for an antiulcer peptide at G. D. Searle in 1965. Although this compound was known in the literature, its sweet taste was serendipitously discovered when a chemist licked his finger which was contaminated with it. Many analogues, especially the more stable esters, were made (6) and their taste qualities and potencies determined. It was the first compound to be chosen for commercial development. Following the purchase of G. D. Searle by Monsanto, the aspartame business was split off to become a separate Monsanto subsidiary called the NutraSweet Company. 

FIGURE 1-23 Stereoisomers distinguishable by smell and taste in humans, (a) Two stereoisomers of carvone R) carvone (isolated from spearmint oil) has the characteristic fragrance of spearmint (S)-carvone (from caraway seed oil) smells like caraway, (b) Aspartame, the artificial sweetener sold under the trade name NutraSweet, is easily distinguishable by taste receptors from its bitter-tasting stereoisomer, although the two differ only in the configuration at one of the two chiral carbon atoms. 

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