Klassische Synthese von Thymopoietin 32-36 (TP 5) unter Verwendung der säurelabilen 1- (1 -Adamantyl) -1 -methylethoxycarbonyl- Schutzgruppe+ / Conventional Synthesis of Thymopoietin 32-36 (TP 5) Using the 1 -(1 - Adamantyl)-1 -methylethoxycarbonyl Group
Abstract:A synthesis of high yields of TP 5 is described. The a-amino functions were blocked by the acid-labile 1-(1 -adamantyl)-1-methylethoxycarbonyl-(Adpoc)group. The Adpoc group is cleaved under mild acidolytic conditions with 3% TFA in CH2CI2 while the tert-butyl residues remained intact. This selective cleavage of the Adpoc group compared with the Boc and tert-butyl residues allows new strategies for the synthesis of large peptides
Die Titelverbindung (IVb), ein immunwirksames Polypeptid, wird nach klassischen Methoden vom C‐terminalen Ende her, ausgehend vom Tyrosinderivat (I), aufgebaut.
Die Titelverbindung (IVb), ein immunwirksames Polypeptid, wird nach klassischen Methoden vom C‐terminalen Ende her, ausgehend vom Tyrosinderivat (I), aufgebaut.
Selective reagents for the removal of the Adpoc group have been developed. For this purpose several peptides containing tryptophan and NE-Boc-lysine have been synthesized. Among several acidolytic reagents, 0.1 N HC1/TFEt/CHC13 (1:9: 1) and 50% HCOOH/TFEt/CHC13 (1 :9: 1) show high selectivity especially for the NE-tert-butyloxycarbonyl group of lysine. Cleavage rates are determined by HPLC and TLC.
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