title: psi(SO2NH) transition state isosteres of peptides. Synthesis and bioactivity of sulfonamido pseudopeptides related to carnosine.
abstract: This paper reports the synthesis of tauryl dipeptides related to carnosine. In particular H-Tau-His-OH (5), H-Tau-His(pi-Me)-OH (6) and H-Tau-His(tau-Me)-OH (9) are described. The enzyme carnosinase has been isolated from pig kidney and after purification has been used to test the stability and the inhibitory activity of the three new analogues. H-Tau-His-OH (5) and H-Tau-His(tau-Me)-OH (9) were found to possess weak inhibitory properties towards carnosinase, while H-Tau-His(pi-Me)-OH (6) proved to be devoid of any significant activity. All the three sulfonamido pseudopeptides 5, 6 and 9 show stability to carnosinase activity.
authors.affiliation: Dipartimento di Studi Farmaceutici, Università La Sapienza, Rome, Italy.
authors.forename: A
authors.initials: A
authors.lastname: Calcagni
authors.forename: P G
authors.initials: PG
authors.lastname: Ciattini
authors.forename: A
authors.initials: A
authors.lastname: Di Stefano
authors.forename: S
authors.initials: S
authors.lastname: Duprè
authors.forename: G
authors.initials: G
authors.lastname: Luisi
authors.forename: F
authors.initials: F
authors.lastname: Pinnen
authors.forename: D
authors.initials: D
authors.lastname: Rossi
authors.forename: A
authors.initials: A
authors.lastname: Spirito
mesh_terms: D002336:Carnosine / Q000031:analogs & derivatives*; D004150:Dipeptidases / Q000037:antagonists & inhibitors*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D004151:Dipeptides; D004791:Enzyme Inhibitors; D002336:Carnosine; D004150:Dipeptidases; C019673:aminoacyl-histidine dipeptidase