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New tris‐alkoxycarbonyl arginine derivatives for peptide synthesis
Author(s) -
Izdebski Jan,
Gers Tomasz,
Kunce Danuta,
Markowski Paweł
Publication year - 2005
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.585
Subject(s) - dermorphin , chemistry , tris , arginine , peptide , peptide synthesis , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , amino acid , biochemistry , receptor , opioid peptide , opioid
α‐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 α, ω, ω′ ‐tris‐alkoxycarbonyl arginines. Two of them, Boc‐Arg‐{ω,ω′‐[Z(2Br)] 2 }‐OH and Boc‐Arg‐{ω,ω′‐[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 © 2004 European Peptide Society and John Wiley & Sons, Ltd.