psi(SO2NH) transition state isosteres of peptides. Synthesis and bioactivity of sulfonamido pseudopeptides related to carnosine.
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.
Calcagni
A
A
Dipartimento di Studi Farmaceutici, Università La Sapienza, Rome, Italy.
Ciattini
P G
PG
Di Stefano
A
A
Duprè
S
S
Luisi
G
G
Pinnen
F
F
Rossi
D
D
Spirito
A
A
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
D004151:Dipeptides; D004791:Enzyme Inhibitors; D002336:Carnosine; D004150:Dipeptidases; C019673:aminoacyl-histidine dipeptidase