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Microwave-assisted guanidinylation in solid phase peptide synthesis: comparison of various reagents
Authors:Ewa Witkowska  Karolina KubikJolanta Krosnicka  Karolina GrabowskaAnna Niescioruk  Beata WilenskaAleksandra Misicka
Institution:Faculty of Chemistry, Biological and Chemical Research Center, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
Abstract:The guanidinylation of a peptide chain on a polymeric support under microwave conditions using derivatives of thioureas—S-alkylisothioureas, pyrazole-carboxamidine, and guanidine as guanidinylating reagents is described. The best results are obtained with N,N′-di-Z-S-methylisothiourea and N,N′-di-Z(2-Cl)-S-methylisothiourea. It is found that guanidinylation with reagents containing Boc groups is accompanied by side reactions.
Keywords:Boc  tert-butyloxycarbonyl  Dab  2  4-diaminobutyric acid  Dap  2  3-diaminopropionic acid  Dap(g)  3-guanidino-2-aminopropionic acid  DIC  1  3-diisopropylcarbodiimide  DIEA  diisopropylethylamine  hArg(g)  2  6-diguanidinohexanoic acid  MW  microwave  TBTU  2(1H-benzotriazole-1-yl)-1  1  3  3-tetramethyluronium tetrafluoroborate  TFA  trifluoroacetic acid  TIS  triisopropylsilane  Z  benzyloxycarbonyl  Z(2-Cl)  2-chlorobenzyloxycabonyl
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