Synthetic sweeteners. 3. Aspartyl dipeptide esters from L- and D-alkylglycines

Mazur, Robert H.; Reuter, Judith A.; Swiatek, Kenneth A.; Schlatter, James M.

doi:10.1021/jm00269a014

Cited by 75 publications

(26 citation statements)

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“…Another group possibly involved in the interaction of aspartame with the sweetness receptor is the methyl carboxylate group (COOCH 3 ) denoted as an E] binding site following the terminology proposed by Tinti and Nofre (1991) for the binding sites of sweeteners. In fact, the interaction of this group is not essential to the sweetness of this dipeptide since the replacement of the COOCH3 group of aspartame (Figure 4a) by a CH 3 group leads to a compound (Figure 4b) which is still about 50 times sweeter than sucrose in man (Mazur et al, 1970(Mazur et al, , 1973. Consequently, in aspartame, the COOCH 3 group must be considered as only a sweetness amplifying group, increasing the sweetness potency by a factor of about 3.5 in comparison with a CH 3 group.…”

Section: Discussionmentioning

confidence: 99%

Evolution of the Sweetness Receptor in Primates. I. Why Does Alitame Taste Sweet in all Prosimians and Simians, and Aspartame only in Old World Simians?

1995

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In the order Primates the responses to sucrose, alitame and aspartame were ascertained. All primates tested to date like sucrose and prefer this sweet substance to tap water. The artificial dipeptide aspartame was found to be not sweet in Prosimii and Platyrrhini (New World monkeys). Only the Cercopithecoidea (Old World monkeys) and Hominoidea (apes and humans) show the same response to aspartame and to sucrose. In contrast, all primates tested so far prefer alitame, another artificial dipeptide sweetener, which is structurally closely related to aspartame. This phylogenetic difference is consistent with the existence in catarrhine primates of a sweetness receptor containing two differently located hydrophobic recognition sites, one for the hydrophobic binding site of alitame, the other for the hydrophobic binding site of aspartame. On the basis of these results, it is suggested that the alitame-related hydrophobic recognition site, which is found in the sweetness receptor of all primates, could be a requisite for the interaction of the receptor with sucrose, while the aspartame-related hydrophobic recognition site, which is found exclusively in the sweetness receptor of Old World simians, could have been a crucial factor in the improvement in detection or selection of sucrose in foods, so favouring the mental development of these simians and maybe the emergence of humans.

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Section: Discussionmentioning

confidence: 99%

Evolution of the Sweetness Receptor in Primates. I. Why Does Alitame Taste Sweet in all Prosimians and Simians, and Aspartame only in Old World Simians?

1995

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“…More interesting was the case of L-Asp-L-Nva-OMe.14) Since the sizes of COOCH3 and CH2CH2CH3 are almost equal, both a sweet formula (17) and a nonsweet formula (18) could be drawn for the dipeptide, so that it could be predicted that the peptide would be slightly sweet. Actually, it was only 4 times sweeter than sucrose.…”

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confidence: 99%

The structure-taste relationships of aspartyl dipeptide esters.

Ariyoshi

1976

Agricultural and Biological Chemistry

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The molecular features common to sweet-tasting dipeptide esters are described. The molecular features of sweet amino acids were represented by the Fischer projection formulas and sweet peptides were related to the sweet amino acids through the Fischer projection formulas of the peptides. It was concluded that a peptide is sweet when it takes the formula 5a, whereas when it takes the formula Sb it is not sweet. It was also concluded that a third binding site (R1 in 5a) besides the postulated AH-B system in a sweet molecule is necessary for an intense sweetness potency. The location of the site in the molecule relative to the AH B system is important, as well as the shape and size of this site, because the third binding site is considered to participate in hydrophobic interaction with a similar binding site on the taste receptor. Increased sweetness is observed when these require ments are satisfied. At present, the phenomenon of taste seems

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“…3, Table 3) Dependent property: Log(RS), values taken from literature [18][19][20][21][22][23][24][25][26][27][28][29][30][31] Training set: 33 molecule (Table 3, The prediction for the training set molecules is very good (F and K CV have high values). The prediction for the testing set molecules is poorer (K = 0.5714).…”

Section: Qsar Study #3mentioning

confidence: 99%

Sweetness power QSARs by PRECLAV software

Tarko¹,

Lupescu²,

Diana³

2005

Arkivoc

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This paper presents some QSAR (Quantitative Structure Activity Relationship) studies with a testing set, realized by the PRECLAV (Property Evaluation by Class Variables) computer program. The database we used contains sweeteners with very diverse structures -sugars, halosugars, guanidine derivatives and 3-aminosuccinamic acid derivatives. According to their estimated values of Log(RS), the testing set molecules are classified as "recommended", "uncertain", or "un-recommended" for synthesis. Comparing the estimated Log(RS) values with the observed values we have found that the aforementioned classification is sufficiently correct to have actual practical value, even if the training/testing set contains sweeteners of several different classes. The N-phenyl-guanidine-acetic acid derivatives, with a polycyclic system bonded with the nitrogen atom, represent a distinct subclass of guanidinic sweeteners.

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Synthetic sweeteners. 3. Aspartyl dipeptide esters from L- and D-alkylglycines

Cited by 75 publications

References 0 publications

Evolution of the Sweetness Receptor in Primates. I. Why Does Alitame Taste Sweet in all Prosimians and Simians, and Aspartame only in Old World Simians?

Evolution of the Sweetness Receptor in Primates. I. Why Does Alitame Taste Sweet in all Prosimians and Simians, and Aspartame only in Old World Simians?

The structure-taste relationships of aspartyl dipeptide esters.

Sweetness power QSARs by PRECLAV software

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