Aspartame analogues containing 1-amino-2-phenylcyclohexanecarboxylic acids (c6Phe)

  1. Avenoza, A. 1
  2. París, M. 1
  3. Peregrina, J.M. 1
  4. Alías, M. 2
  5. López, M.P. 2
  6. García, J.I. 2
  7. Cativiela, C. 2
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Zeitschrift:
Tetrahedron

ISSN: 0040-4020

Datum der Publikation: 2002

Ausgabe: 58

Nummer: 24

Seiten: 4899-4905

Art: Artikel

DOI: 10.1016/S0040-4020(02)00435-0 SCOPUS: 2-s2.0-0037054222 WoS: WOS:000176179800017 GOOGLE SCHOLAR

Andere Publikationen in: Tetrahedron

Institutionelles Repository: lock_openOpen Access Editor

Zusammenfassung

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of aspartame: H-(S)-Asp-(1R,2R)-c6Phe-OMe and H-(S)-Asp-(1S,2S)-c6Phe-OMe, in which the Phe residue of aspartame has been replaced by a restricted Phe with a cyclohexane skeleton: 1-amino-2-phenylcyclohexanecarboxylic acid (c6Phe).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.