SYNTHESIS OF TRANS-5-METHYLPROLINE AND ITS INFLUENCE ON CIS-TRANS-ISOMERISM IN BETA-CASOMORPHIN-5

Authors
TOURWE D VANBETSBRUGGE J VERHEYDEN P HOOTELE C
Citation
D. Tourwe et al., SYNTHESIS OF TRANS-5-METHYLPROLINE AND ITS INFLUENCE ON CIS-TRANS-ISOMERISM IN BETA-CASOMORPHIN-5, Bulletin des Societes chimiques belges, 103(5-6), 1994, pp. 201-205
Citations number
17
Categorie Soggetti
Chemistry
Journal title
Bulletin des Societes chimiques belges → ACNP
ISSN journal
00379646
Volume
103
Issue
5-6
Year of publication
1994
Pages
201 - 205
Database
ISI
SICI code
0037-9646(1994)103:5-6<201:SOTAII>2.0.ZU;2-9
Abstract
Starting from L-proline, trans-5-methylproline has been prepared using electrochemical oxidation followed by methylcopper substitution. Afte r incorporation of this amino acid into beta-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 d id not allow to confirm the requirement for a cis Tyr-Pro peptide bond for biological activity.