Die Synthese eines Tetracosapeptides mit der Aminosäuresequenz eines hochaktiven Abbauproduktes des β-Corticotropins (ACTH) aus Schweinehypophysen. (Vorläufige Mitteilung)

作者: H. Kappeler , R. Schwyzer

DOI: 10.1002/HLCA.19610440436

关键词: HydrolysateStereochemistryPeptideChemistryTrifluoroacetic acidTetracosapeptideAmino acid residueYield (chemistry)

摘要: A tetracosapeptide (11) incorporating the amino acid residues 1–24 of β-corticotropin has been synthesized. This peptide was held responsible for ACTH-activity in hydrolysates porcine β-corticotropin, but never isolated therefrom. The synthesis made possible by using Ne -t-butoxycarbonyl-L-lysine and γ-t-butyl-L-glutamate as intermediates. number other key-intermediates were prepared their p-phenylazo-benzyloxy-carbonyl derivatives, colour facilitating purification. As preparation an analogous nonadecapeptide, last condensation involved a crystalline derivative decapeptide sequence 1–10. Removal all protecting groups step (t-butoxy-carbonyl- t-butoxy-) effected quantitative yield dissolution trifluoroacetic acid.

参考文章(4)
R. Schwyzer, W. Rittel, H. Kappeler, B. Iselin, Synthese eines Nanadeka-peptides mit hoher corticotroper Wirksamkeit Angewandte Chemie. ,vol. 72, pp. 915- 917 ,(1960) , 10.1002/ANGE.19600722308
R. Schwyzer, P. Sieber, K. Zatskó, Farbige Schutzgruppen für die Synthese von Polypeptiden Helvetica Chimica Acta. ,vol. 41, pp. 491- 498 ,(1958) , 10.1002/HLCA.660410222
R. G. Shepherd, S. D. Willson, K. S. Howard, P. H. Bell, D. S. Davies, S. B. Davis, E. A. Eigner, N. E. Shakespeare, Studies with Corticotropin. III. Determination of the Structure of β-Corticotropin1 and its Active Degradation Products Journal of the American Chemical Society. ,vol. 78, pp. 5067- 5076 ,(1956) , 10.1021/JA01600A067
Howard Sachs, Erwin Brand, Benzyl Esters of Glutamic Acid1 Journal of the American Chemical Society. ,vol. 75, pp. 4610- 4611 ,(1953) , 10.1021/JA01114A529