Ψ(SO2NH) transition state isosteres of peptides.: Synthesis and bioactivity of sulfonamido pseudopeptides related to carnosine

被引：13

作者：

Calcagni, A

Ciattini, PG

Di Stefano, A

Duprè, S

Luisi, G

Pinnen, F

Rossi, D

Spirito, A

机构：

[1] Univ G Annunzio, Ist Sci Farmaco, I-66100 Chieti, Italy

[2] Univ Rome La Sapienza, Dipartimento Studi Farmaceut, I-00185 Rome, Italy

[3] Univ Rome La Sapienza, Ctr Studi Chim Farmaco, CNR, I-00185 Rome, Italy

[4] Univ Rome La Sapienza, Dipartimento Sci Biochim, I-00185 Rome, Italy

来源：

FARMACO | 1999年 / 54卷 / 10期

关键词：

carnosinase inhibitors; carnosine; sulfonamido peptides; taurine; transition state;

D O I：

10.1016/S0014-827X(99)00079-8

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

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-Kis(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. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：673 / 677

页数：5

共 32 条

[1] L-CARNOSINE (BETA-ALANYL-L-HISTIDINE) AND CARCININE (BETA-ALANYLHISTAMINE) ACT AS NATURAL ANTIOXIDANTS WITH HYDROXYL-RADICAL-SCAVENGING AND LIPID-PEROXIDASE ACTIVITIES [J].