83595-75-9Relevant academic research and scientific papers
Syntheses and biological activities of bombesin analogs modified in the C-terminal dipeptide part
Llinares,Devin,Azay,Berge,Fehrentz,Martinez
, p. 767 - 780 (2007/10/03)
Bombesin receptor antagonists are possible therapeutic agents due to their ability to act as inhibitors of cellular proliferation. On the basis of our hypothesis on the mechanism of action of gastrin associating an activating enzyme system to the receptor and on the results reported in the litterature, we have synthesized bombesin analogues which have been modified in the C-terminal Leu13-Leu14 amide part. We have shown that modification in the C-terminal part of the bombesin strongly affected the biological activity in rat pancreatic acini. The most potent compound which is described here, H-D-Phe-Gln-Trp-Ala-Val-Gly-His-Leu-Ψ/(CH2)Leu-NH2, was able to recognize the bombesin receptor on rat pancreatic acini (Ki 4.3 nM) and antagonized the bombesin stimulated amylase secretion (Ki 7.7 nM).
New Protecting Groups for the Indole Ring of Tryptophan in Peptide Synthesis: 2,4,6-Trimethoxybenzenesulfonyl and 4-Methoxy-2,3,6-trimethylbenzenesulfonyl Groups
Fukuda, Tsunehiko,Wakimasu, Mitsuhiro,Kobayashi, Shigeru,Fujino, Masahiko
, p. 2825 - 2835 (2007/10/02)
Five substituted benzenesulfonyl groups, p-toluenesulfonyl, p-methoxybenzenesulfonyl, 2,4-dimethoxybenzenesulfonyl, 2,4,6-trimethoxybenzenesulfonyl, and 4-methoxy-2,3,6-trimethylbenzenesulfonyl, were introduced at Nin of tryptophan and their protecting group properties were investigated.Among them, 2,4,6-trimethoxybenzenesulfonyl and 4-methoxy-2,3,6-trimethylbenzenesulfonyl are stable to trifluoroacetic acid, but can be readily removed by hydrogen fluoride or methanesulfonic acid, and suppress decomposition and modification of the tryptophan residue during peptide synthesis.These protecting groups were successfully used in syntheses of bombesin, a potent analog of luteinizing hormone-releasing hormone by the solution method and dynorphin by the solid-phase method.Keywords-peptide synthesis; tryptophan; protecting group; 2,4,6-trimethoxybenzenesulfonyl group; 4-methoxy-2,3,6-trimethylbenzenesulfonyl group
