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  • 1
    ISSN: 1075-2617
    Keywords: conformational analysis ; NMR spectroscopy ; X-ray diffraction ; peptide-based taste ligands ; artificial sweeteners ; computer simulations ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A dipeptide taste ligand L-aspartyl-D-2-aminobutyric acid-(S)-α-ethylbenzylamide was found to be about 2000 times more potent than sucrose. To investigate the molecular basis of its potent sweet taste, we carried out conformational analysis of this molecule and several related analogues by NMR spectroscopy, computer simulations and X-ray crystallographic studies. The results of the studies support our earlier model that an ‘L’-shape molecular array is essential for eliciting sweet taste. In addition, we have identified an aromatic group located between the stem and the base of the ‘L-shape’, which is responsible for enhancement of sweetness potency. In this study, we also assessed the optimal size of the essential hydrophobic group (X) and the effects of the chirality of the second residue toward taste. ©1997 European Peptide Society and John Wiley & Sons, Ltd.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1075-2617
    Keywords: Conformational analysis ; peptide-based taste ligands ; artificial sweeteners ; X-ray crystal structures ; Chemistry ; Biochemistry and Biotechnology
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The molecular basis of sweet taste was investigated by carrying out the crystal state conformational analysis by X-ray diffraction of the following dipeptide taste igands:N-3,3-dimethylbutyl-aspartyl-phenylalanine methyl ester,I(N-DMB-Asp-Phe-OMe), its sodium salt (N-DMB-Asp-Phe-ONa),II, aspartyl-D-2-aminobutyric acid-(S)-α-ethylbenzylamide,III(Asp-D-Abu-(S)-α-ethylbenzylamide), aspartyl-N′-((2,2,5,5-tetramethylcyclopentanyl)-carbonyl)-(R)-1,1-diamino-ethane,IV(Asp-(R)-gAla-TMCP), and aspartyl-D-valine-(R)-α-methoxymethylbenzyl amide,V(Asp-D-Val-(R)-α-methoxymethylbenzylamide). With the exception of the sodium saltII, all compounds are sweet-tasting, showing in some cases considerable potency enhancement with respect to sucrose. The results of this study confirm the earlier model that an ‘L-shape’ molecular array is essential for eliciting sweet taste for dipeptide-like ligands. In addition, it was established that (i) substitution of the N-terminal group does not inhibit sweet taste, if its zwitterionic character is maintained; (ii) a hydrophobic group located between the stem and the base of the L-shape could be responsible for sweetness potency enhancement, as found inI, IIIandIV; in fact, the extraordinary potency of the N-alkylated analogueIwould support a model with an additional hydrophobic binding domain above the base of the ‘L’; (iii) removal of the methyl ester at the C-terminus of compoundIwith the salt formation gives rise to the tasteless compoundII; (iv) for the first time all possible side-chain conformers (g-,g+andt) for the N-substituted aspartyl residue were observed; and (v) a retro-inverso modification, incorporated at position 2 of the dipeptide chain, confers greater flexibility to the molecule, as demonstrated by the contemporary presence of six conformationally distinct independent molecules in the unit cell and yet sweet taste properties are maintained, as found inIV. © 1998 European Peptide Society and John Wiley & Sons, Ltd.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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