Aspartame analogues containing 1-amino-2-phenylcyclohexanecarboxylic acids (c6Phe)
- Avenoza, A. 1
- París, M. 1
- Peregrina, J.M. 1
- Alías, M. 2
- López, M.P. 2
- García, J.I. 2
- Cativiela, C. 2
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1
Universidad de La Rioja
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2
Instituto de Nanociencia y Materiales de Aragón
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ISSN: 0040-4020
Any de publicació: 2002
Volum: 58
Número: 24
Pàgines: 4899-4905
Tipus: Article
Altres publicacions en: Tetrahedron
Resum
This report describes the synthesis and the conformational analysis of the optically pure dipeptides analogues of aspartame: H-(S)-Asp-(1R,2R)-c6Phe-OMe and H-(S)-Asp-(1S,2S)-c6Phe-OMe, in which the Phe residue of aspartame has been replaced by a restricted Phe with a cyclohexane skeleton: 1-amino-2-phenylcyclohexanecarboxylic acid (c6Phe). Of these, only the dipeptide that incorporates (1R,2R)-c6Phe is sweet, whereas that incorporates (1S,2S)-c6Phe is bitter. This relationship between the absolute configuration of the dipeptides and the properties is explained through the different conformational behaviour displayed by each molecule, based on molecular mechanics and molecular dynamics calculations, including solvent effects. © 2002 Elsevier Science Ltd. All rights reserved.