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Synthesis and Biological Activity of Homoarginine-Containing Opioid Peptides

Synthesis and Biological Activity of Homoarginine-Containing Opioid Peptides

Jan Izdebski, Danuta Kunce, Peter W Schiller, Nga N Chung, Tomasz Gers, Monika Zelman, Monika Grabek

J Pept Sci. 2007 Jan;13(1):27-30.

PMID: 16967435

Abstract:

Two tris-alkoxycarbonyl homoarginine derivatives, Boc-Har{omega,omega'-[Z(2Br)]2}-OH and Boc-Har{omega,omega'-[Z(2Cl)]2}-OH, were prepared by guanidinylation of Boc-Lys-OH, and used for the synthesis of neo-endorphins and dynorphins. The results were compared with that obtained in the synthesis in which Boc-Lys(Fmoc)-OH was incorporated into the peptide chain, and after removing Fmoc protection, the resulting peptide-resin was guanidinylated with N,N'-[Z(2Br)]2- or N,N'-[Z(2Cl)]2-S-methylisourea. The peptides were tested in the guinea-pig ileum (GPI) and mouse vas deferens (MVD) assays. The results indicated that replacement of Arg by Har may be a good avenue for the design of biologically active peptides with increased resistance to degradation by trypsin-like enzymes.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP20887950	Boc-Cys-OH		20887-95-0	Price

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