title: Stability against enzymatic hydrolysis of endomorphin-1 analogues containing beta-proline.
abstract: The enantiomer of endomorphin-1 (Tyr-Pro-Trp-PheNH2) and the analogues containing (S)- or (R)-beta-proline have been synthesized, and their affinities towards mu-opioid receptors have been measured. As expected, the incubations of the different peptides with some commercially available enzymes showed that the presence of D-residues gave strong resistance towards digestion. The presence of beta-proline alone is sufficient to confer good resistance against the hydrolysis of the biologically strategic Pro-Trp bond.
authors.affiliation: Dipartimento di Chimica G. Ciamician, Università di Bologna, via Selmi 2, 40126 Bologna, Italy. cardillo@ciam.unibo.it
authors.forename: Giuliana
authors.initials: G
authors.lastname: Cardillo
authors.forename: Luca
authors.initials: L
authors.lastname: Gentilucci
authors.forename: Alessandra
authors.initials: A
authors.lastname: Tolomelli
authors.forename: Maria
authors.initials: M
authors.lastname: Calienni
authors.forename: Ahmed R
authors.initials: AR
authors.lastname: Qasem
authors.forename: Santi
authors.initials: S
authors.lastname: Spampinato
mesh_terms: D000818:Animals; D018826:CD13 Antigens / Q000378:metabolism; D002268:Carboxypeptidases / Q000378:metabolism; D002918:Chymotrypsin / Q000378:metabolism; D006868:Hydrolysis; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D011392:Proline / Q000737:chemistry*; D051381:Rats; D017450:Receptors, Opioid, mu / Q000819:agonists; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry
chemical_list: D009842:Oligopeptides; D017450:Receptors, Opioid, mu; C105293:endomorphin 1; D014364:Tryptophan; D011392:Proline; D002268:Carboxypeptidases; D018826:CD13 Antigens; D002918:Chymotrypsin