Aspartame dipeptide analogues: effect of number of side-chain methylene group spacers and Cα-methylation in the second position
Tetrahedron AsymmetryPublished 1 April 1997
E. Mossel, Fernando Formaggio, Marco Crisma, Claudio Toniolo, Quirinus B. Broxterman, Wilhelmus H. J. Boesten
Citations38
Generate an AI Snapshot to get a quick, structured summary of this paper.
Study Snapshot
ObjectiveStudy objective
MethodsResearch methodology
PopulationPopulation studied
Sample sizeSample sizes
OutcomesStudy outcomes here
ResultsStudy results comes here
LimitationsResearch study limitations comes here
A concise AI-generated summary of the paper will appear here once you click Generate AI Snapshot.
Abstract
Our model of the active site of the sweet taste receptor is shown to be consistent with the aspartame analogues in which the L-Phe(2) residue is replaced by L-(alpha Me)Phg, L-(alpha Me)Phe or L-(alpha Me)Hph. The analogues containing either the first or the third C-alpha-methylated, phenyl-containing residue in the second position of the dipeptide were synthesized and found to be approximately as sweet as aspartame itself and its L-(alpha Me)Phe(2) analogue. (C) 1997 Elsevier Science Ltd.
Keywords
ChemistryNursingBiochemistry, Genetics and Molecular Biology
Journal of the American Chemical SocietyA new force field for molecular mechanical simulation of nucleic acids and proteins
4,617 Citations1984Scott J. Weiner, Peter A. Kollman +6 more
The development of a force field for simulation of nucleic acids and proteins is presented and considerable effort has been placed in developing analytical functions that are simple enough to allow one to simulate the properties of complex molecules yet accurate enough to obtain meaningful estimates for structures and energies.
Journal of Computational ChemistryAn all atom force field for simulations of proteins and nucleic acids
3,440 Citations1986Scott J. Weiner, Peter A. Kollman +2 more
An all atom potential energy function for the simulation of proteins and nucleic acids and the first general vibrational analysis of all five nucleic acid bases with a molecular mechanics potential approach is presented.
Journal of the American Chemical Society1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive
1,462 Citations1993Louis A. Carpino
Journal of the American Chemical SocietyStructure-taste relationships of some dipeptides
275 Citations1969Robert H. Mazur, James M. Schlatter +1 more
BiopolymersStructures of peptides from α‐amino acids methylated at the α‐carbon,
240 Citations1993Claudio Toniolo, Marco Crisma +6 more
The Journal of Organic ChemistrySynthesis of optically pure .alpha.-alkylated .alpha.-amino acids and a single-step method for enantiomeric excess determination
148 Citations1988W. Kruizinga, John Bolster +5 more
Helvetica Chimica ActaSynthèse d'analogues structuraux de l'oxytocine
110 Citations1956R. A. Boissonnas, St. Guttmann +2 more
The syntheses of four analogues of oxytocine are described and one with a phenylalanyl residue replacing the isoleucyl residue is synthesised.
Aspartame: Physiology and Biochemistry
105 Citations1984Lewis D. Stegink, L. J. Filer
This monograph discusses the history and background discovery of Aspartame, its use in human and non-primate animals, and its implications for the Food Scientist.
Tetrahedron AsymmetryEnzymatic resolution of α,α-disubstituted α-amino acid esters and amides
89 Citations1993Bernard Kaptein, Wilhelmus H. J. Boesten +4 more
The scope and limitations of the enzymatic resolution of α,α-disubstituted α-amino acid amides by an amino acid amidase from Mycobacterium neoaurum and of the corresponding ethyl esteis with Pig liver estetase (PLE) have been studied.
Journal of the American Chemical SocietyCrystal structure of aspartame, a peptide sweetener
67 Citations1985Marcos Hatada, Jarmila Jancarik +2 more
Journal of Medicinal ChemistryThree-dimensional mapping of the sweet taste receptor site
57 Citations1978Piero Andrea Temussi, Francesco Lelj +1 more
The active sites of the receptors for sweet and bitter tastants are shown to be related by a simple symmetry operation, which allows the identification of the critical geometrical features of both receptor sites.
Journal of Medicinal ChemistryStructure-taste correlation of L-aspartyl dipeptides using the SIMCA method
56 Citations1986Yoshikatsu Miyashita, Yoshimasa Takahashi +6 more
Angewandte Chemie International Edition in EnglishConformational Requirements for Sweet‐Tasting Peptides and Peptidomimetics
46 Citations1994Toshimasa Yamazaki, Ettore Benedetti +2 more
The topochemical requirements of the sweet and bitter taste receptor(s) are described and detailed structure-taste relationships with considerable predictive power for peptides and related molecules are developed.
Bioorganic & Medicinal Chemistry LettersNew aspartame-like sweeteners containing L-(αMe)Phe
43 Citations1992Stefano Polinelli, Quirinus B. Broxterman +6 more
The [L-(αMe) Phe] 2 -analogue of aspartame was synthesized and analyzed by X-ray diffraction and fits well within the sweet perception model as developed by Temussi, Toniolo and coworkers.
TetrahedronBioactive and model peptides characterized by the helicogenic (αMe)Phe residue
41 Citations1993Claudio Toniolo, Fernando Formaggio +8 more
The hypersweet super-aspartame analogue p CN-C6H4-NHCO-L-Asp-L-(αMe)Phe-OME 1, the first D-chemotactic peptide being found more active than its L-diastereomer, is synthesized and fully characterized.
Pure and Applied ChemistryChemo-enzymatic synthesis of amino acids and derivatives
38 Citations1992H. Schoemaker, Wilhelmus H. J. Boesten +6 more
Two enzymes, an aminopeptidase from Pseudomonas putida and an amidase from Hycobacterium neoaurum have been purified to homogeneity and methods for the stereoselective synthesis of a-alkyl-substituted hydroxy acids are given.
Journal of Medicinal ChemistryConformation-activity relationship of sweet molecules. Comparison of aspartame and naphthimidazolesulfonic acids
37 Citations1990Maria Antonietta Castiglione Morelli, Francesco Lelj +4 more
The results indicate that the minimum-energy conformation for aspartame in water, DMSO-d6, and CDCl3 (as a crown ether complex) is different from that originally proposed (FIIDII instead of FIDII, according to a notation referred to the side chains).
Journal of Medicinal ChemistryHigh potency dipeptide sweeteners. 1. L-Aspartyl-D-phenylglycine esters
29 Citations1990John M. Janusz, J. M. GARDLIK +5 more
Twenty esters of L-aspartyl-D-phenylglycine, as well as two substituted analogues, an o-fluoro and a p-hydroxy- Phenyl Glycine ester, were prepared and the high potency of these sweeteners is surprising.
Journal of Peptide ScienceSweet and bitter taste: Structure and conformations of two aspartame dipeptide analogues
27 Citations1995Ettore Benedetti, E. Gavuzzo +6 more
Conformational analysis of the two taste ligands in solution by NMR and computer simulations agrees well with the model for sweet and bitter tastes.
BiopolymersEffect of phenyl ring position in the Cα-methylated α-amino acid side chain on peptide preferred conformation
18 Citations1996Claudio Toniolo, Marco Crisma +7 more
This study shows that β‐turn and 310‐helical structures are preferentially adopted by peptides rich in these Cα‐methylated, aromatic α‐amino acids and turn and helix handedness is critically biased by the position of side‐chain branching.
Journal of Agricultural and Food ChemistryN-Formylcarbamoylaspartame, a new aspartame-like sweetener. Synthesis and studies on stability and biological properties
12 Citations1991Willy H. J. Boesten, Ben H. N. Dassen +6 more
Journal of the Chemical Society Perkin Transactions 2Conformationally restricted analogues of anti-aspartame-type sweeteners
11 Citations1992Fernando Formaggio, Marco Crisma +6 more
International journal of peptide & protein researchStructural versatility of peptides from C<sup>α,α</sup>‐disubstituted glycines: crystal‐state conformational analysis of peptides from C<sup>α</sup>‐methylhomophenylalanine, (αMe)Hph
7 Citations1996Mitsunobu Doi, Toshimasa Ishida +6 more
The molecular and crystal structures of the C alpha-tetrasubstituted, delta-branched alpha-amino acid, H-D-(alpha Me)Hph-OH, and three peptides (to the pentamer level), including the homotripeptide, have been determined by X-ray diffraction.
Journal of Agricultural and Food ChemistryStability of N-Derivatized and .alpha.-Methyl Analogs of Aspartame to Hydrolysis by Mammalian Cell-Surface Peptidases
5 Citations1994Nigel M. Hooper, Richard Hesp +4 more
Of the N-derivatized analogues of APM, only N-formylcarbamoyl-APM was hydrolyzed slightly by the human and porcine intestinal microvillar membrane preparations (1.1 nmol min -1 (mg of protein) -1 for APM with the human jejunal micro Villar membranes).
Journal of the Chemical Society Perkin Transactions 2Linear oligopeptides. Part 352. Synthesis, characterization and solution conformational analysis of C<sup>α</sup>-methyl-homo-phenylalanine [(αMe)Hph] containing peptides
5 Citations1996A. Polese, Fernando Formaggio +5 more
A solution conformational analysis and a CD study of Nαpara-bromobenzoylated peptides suggest that the relationship between (αMe)Hph α-carbon chirality and the prevailing screw sense of the turn and helical structures that are formed is opposite to that found for ( αMe)Phe and (αEt)P he.