Journal of Peptide Science 2005-01-01

New tris-alkoxycarbonyl arginine derivatives for peptide synthesis.

Jan Izdebski, Tomasz Gers, Danuta Kunce, Paweł Markowski

Index: J. Pept. Sci. 11(1) , 60-4, (2005)

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Abstract

alpha-Alkoxycarbonyl protected ornithines were treated with N,N'-[Z(2Cl)](2)-S-methylisothiourea and N,N'-[Z(2Br)](2)-S-methylisothiourea, N,N'-Z(2)-S-methylisothiourea and N,N'-Boc(2)-S-methylisothiourea to form N(alpha, omega, omega')-tris-alkoxycarbonyl arginines. Two of them, Boc-Arg-{omega,omega'-[Z(2Br)](2)}-OH and Boc-Arg-{omega,omega'-[Z(2Cl)](2)}-OH, were used for the synthesis of dermorphin fragments containing two or three arginine residues. Examination of the products by HPLC and ESI-MS revealed that the purity of the materials obtained with the use of the new derivatives was higher than that obtained in concurrent syntheses in which Boc-Arg(Tos) was used.Copyright (c) 2004 European Peptide Society and John Wiley & Sons, Ltd.