Synthesis and charge-transfer properties of two acth analogues containing pentamethylphenylalanine in position 9.
In order to investigate the possible role of the Trp residue in ACTH as a change-transfer donor in the activation of ACTH receptors, two ACTH analogues (beta-corticotrophins (I-24) with L-Ser1 and D-Ser1, respectively) containing pentamethylphenylalanine instead of Trp have been synthesized. In these syntheses a new, alkaline-labile, amino-protecting group, the methylsulphonylethyloxycarbonyl group, was employed. The association constants of ACTH (I-24) and (Pmp9)-ACTH (I-24) with the water-soluble acceptor paraquat, were nearly equal.
D000107:Acetylation; D000324:Adrenocorticotropic Hormone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002845:Chromatography; D003460:Crystallization; D005374:Filtration; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D010269:Paraquat; D010649:Phenylalanine / Q000031:analogs & derivatives; D011485:Protein Binding; D013696:Temperature; D014364:Tryptophan
D010649:Phenylalanine; D014364:Tryptophan; D000324:Adrenocorticotropic Hormone; D010269:Paraquat