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Synthesis of Trans‐5‐Methylproline and its Influence on CIS‐Trans Isomerism in β‐Casomorphin‐5

par Tourwe, Dirk ;van Betsbrugge, Jo;Verheyden, Patricia;Hootele, Claude
Référence Bulletin des Sociétés chimiques belges, 103, 5-6, page (201-205)
Publication Publié, 1994

Article révisé par les pairs

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Résumé :

Starting from L‐proline, trans‐5‐methylproline has been prepared using electrochemical oxidation followed by methylcopper substitution. After incorporation of this amino acid into β‐casomorphin‐5 at the two and four position, an NMR study revealed only limited influence on the cis/trans ratio of the peptide bond. The opioid receptor affinities did not allow to confirm the requirement for a cis Tyr‐Pro peptide bond for biological activity. Copyright © 1994 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim