New tris-alkoxycarbonyl arginine derivatives for peptide synthesis.
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.
Izdebski
Jan
J
Peptide Laboratory, Department of Chemistry, Warsaw University, Poland. izdebski@chem.uw.edu.pl
Gers
Tomasz
T
Kunce
Danuta
D
Markowski
Paweł
P
D001120:Arginine / Q000031:analogs & derivatives / Q000737:chemistry*; D004399:Dynorphins / Q000138:chemical synthesis; D008722:Methods; D010446:Peptide Fragments / Q000138:chemical synthesis; D010455:Peptides / Q000138:chemical synthesis*; D013890:Thiourea / Q000031:analogs & derivatives
D010446:Peptide Fragments; D010455:Peptides; C026843:dynorphin (1-13); D004399:Dynorphins; C026770:dynorphin (1-8); D001120:Arginine; D013890:Thiourea