[Investigations on peptide synthesis with polymeric supports: synthesis and characterization of the deamido-calcitonin-M-(19-32)-tetradecapeptide by use of the soluble support polyethyleneglycol and coupling of the products to the insoluble polystyryl-benzhydrylamine resin (author's transl)].
The synthesis of the deamido-calcitonin-M-(19-32)-tetradecapeptide Boc-Phe-His-Thr(Bzl)-Phe-Pro-Gln-Thr(Bzl)-Ala-Ile-Gly-Val-Gly-Ala-Pro-OH (I) by the use of the soluble polymeric support polyethyleneglycol is described. For product characterization the following compounds were prepared:H-Phe-His-Thr(Bzl)-Phe-Pro-Gln-Thr(Bzl)-Ala-Ile-Gly-Val-Gly-Ala-Pro-OH and H-Phe-His-Thr-Phe-Pro-Gln-Thr-Ala-Ile-Gly-Ala-Pro-OH. The analyses of these products by ion exchange chromatography indicates that the correct tetradecapeptide sequence was synthesized to more than 90%. Despite high yields in the coupling reactions, crude I was inhomogenous due to partial cleavage to O-benzyl ether bonds. In order to use I for the total synthesis of calcitonin M, it was coupled to the insoluble polystyryl-benzhydrylamine resin. 0.08 mmol of peptide was coupled per g of resin. Treatment of this peptide resin with hydrogen fluoride yielded H-Phe-His-Thr-Phe-Gln-Thr-Ala-Ile-Gly-Val-Gly-Ala-Pro-NH2.
D002116:Calcitonin / Q000138:chemical synthesis*; D002855:Chromatography, Thin Layer; D008722:Methods; D009842:Oligopeptides / Q000138:chemical synthesis*; D011092:Polyethylene Glycols; D011485:Protein Binding; D012116:Resins, Plant; D012995:Solubility
D009842:Oligopeptides; D012116:Resins, Plant; D011092:Polyethylene Glycols; D002116:Calcitonin
Untersuchungen zur Optimierung der Peptidsynthese an polymeren Trägern, IV[1]. Synthese und Charkterisierung des geschützten Deamido-Calcitonin-M-(19-32)-Tetradecapeptids an dem löslichen Träger Polyäthylenglykol und Kupplung des Syntheseproduckts an den unlöslichen Polystyryl-benzhydrylamin-Träger