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
Argitalpen urtea: 2002
Alea: 58
Zenbakia: 24
Orrialdeak: 4899-4905
Mota: Artikulua
Beste argitalpen batzuk: Tetrahedron
Laburpena
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of aspartame: H-(S)-Asp-(1R,2R)-c6Phe-OMe and H-(S)-Asp-(1S,2S)-c6Phe-OMe, in which the Phe residue of aspartame has been replaced by a restricted Phe with a cyclohexane skeleton: 1-amino-2-phenylcyclohexanecarboxylic acid (c6Phe).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.