Active conformations of neotame and other high-potency sweeteners

Journal of Medicinal Chemistry

Volumn 43, Issue 6, 2000, Pages 1242-1245

  Walters, D Eric ^a   Prakash, Indra ^b   Desai, Nitin ^b  

^a ROSALIND FRANKLIN UNIVERSITY OF MEDICINE AND SCIENCE   (United States)

^b MONSANTO COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTAME DERIVATIVE; SWEETENING AGENT;

ARTICLE; CHEMICAL ANALYSIS; COMPUTER PROGRAM; CONFORMATION; HYDROGEN BOND; MODEL; PHARMACOPHORE;

DIPEPTIDES; GUANIDINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SOFTWARE; SWEETENING AGENTS;

EID: 0034704802     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990501z     Document Type: Article

References (15)

1. Walters, D. E.; DuBois, G. E.; Kellogg, M. S. Design of Sweet and Bitter Tastants. In Mechanisms of Taste Transduction; Simon, S. A., Roper, S. D., Eds.; CRC Press: Boca Raton, FL, 1993; pp 463-478.
2. Mazur, R. H.; Schlatter, J. M.; Goldkamp, A. H. Structure-Taste Relationships of some Dipeptides. J. Am. Chem. Soc. 1969, 91, 2684-2691.
3. Tinti, J.-M.; Nofre, C. Synthetic Sweeteners. Fr. Demande FR 2,533,210, 1984; Chem. Abstr. 1984, 101, 152354k.
4. Tinti, J.-M.; Nofre, C. Design of Sweeteners. A Rational Approach. In Sweeteners: Discovery, Molecular Design, and Chemoreception; Walters, D. E., Orthoefer, F. T., DuBois, G. E., Eds.; American Chemical Society: Washington, DC, 1991; pp 88-99.
5. Nofre, C.; Tinti, J.-M.; Chatzopoulos-Ouar, F. Preparation of (Phenylguanidino)- and [[1-(Phenylamino)ethyl]amino]acetic Acids as Sweeteners. Eur. Pat. Appl. EP 241,395, 1987; Chem. Abstr. 1988, 109, 190047k.
6. Nofre, C.; Tinti, J.-M. N-Substituted Derivatives of Aspartame Useful as Sweetening Agents. U.S. Pat. 5,480,668, 1996; Chem. Abstr. 1996, 112, 235846.
7. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. MacroModel - An Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440-467.
8. Halgren, T. A. Merck Molecular Force Field. I. Basis, Form, Scope, Parametrization, and Performance of MMFF94. J. Comput. Chem. 1996, 17, 490-519.
9. Chang, G.; Guida, W. C.; Still, W. C. An Internal Coordinate Monte Carlo Method for Searching Conformational Space. J. Am. Chem. Soc. 1989, 111, 4379-4386.
10. Qiu, D.; Shenkin, P. S.; Hollinger, F. P.; Still, W. C. The GB/SA Continuum Model for Solvation. A Fast Analytical Method for the Calculation of Approximate Born Radii. J. Phys. Chem. A 1997, 101, 3005-3014.
11. Lelj, F.; Tancredi, T.; Temussi, P. A.; Toniolo, C. Interaction of L-Aspartyl-L-phenylalanine Methyl Ester with the Receptor Site of the Sweet Taste Bud. J. Am. Chem. Soc. 1976, 98, 6669-6675.
12. Castiglione-Morelli, M. A.; Lelj, F.; Naider, F.; Tallon, M.; Tancredi, T.; Temussi, P. A. Conformation-Activity Relationship of Sweet Molecules. Comparison of Aspartame and Naphthimidazolesulfonic Acids. J. Med. Chem. 1990, 33, 514-520.
13. For a review, see: Yamazaki, T.; Benedetti, E.; Kent, D.; Goodman, M. Conformational Requirements for Sweet-Tasting Peptides and Peptidomimetics. Angew. Chem., Int. Ed. Engl. 1994, 33, 1437-1451.
14. Mattern, R.-H.; Amino, Y.; Benedetti, E.; Goodman, M. Conformational Analysis of Potent Sweet Taste Ligands by Nuclear Magnetic Resonance, Computer Simulations and X-ray Diffraction Studies. J. Pept. Res. 1997, 50, 286-299.
15. Goodman, M.; Mattern, R.-H.; Gantzel, P.; Santini, A.; Iacovino, R.; Saviano, M.; Benedetti, E. X-ray Structures of New Dipeptide Taste Ligands. J. Pept. Sci. 1998, 4, 229-238.