Synthese von Zwischenprodukten für den Aufbau corticotrop wirksamer Polypeptide III. Das Decapeptid H·Ser‐Tyr‐Ser‐Met‐Glu‐His‐Phe‐Arg‐Try‐Gly·OH und einige seiner Derivate
1961; Wiley; Volume: 44; Issue: 7 Linguagem: Inglês
10.1002/hlca.19610440723
ISSN1522-2675
Autores Tópico(s)Analytical Chemistry and Chromatography
ResumoThe synthesis of the decapeptide H·Ser‐Tyr‐Ser‐Met‐Glu‐His‐Phe‐Arg‐Try‐Gly·OH t ) which constitutes an essential portion of the corticotropin (ACTH) and α‐melanotropin (α‐MSH) molecules, as well as 4 derivatives thereof (I, II, III, V) is described in detail. The derivative BOC‐Ser‐Tyr‐Ser‐Met‐Glu(OBu 1 )‐His‐Phe‐Arg‐Try‐Gly·OH is, on account of its excellent crystallinity, the easy removability of the protecting groups by mild acid catalysis (BOC‐, ‐OBu t ), and the fact that the C‐terminal amino‐acid residue cannot racemize on condensation with other peptides, an especially useful intermediate for syntheses in the field of the hormones of the pituitary 9,12 ). The introduction of the γ‐ t ‐butyl ester of glutamic acid is a new feature which proves especially valuable in connection with N‐ t ‐butoxycarbonyl‐lysine 3 ) 4 ) 9 ). These protecting groups can be removed even from very complicated peptides by mild acid catalysis in excellent yield which is a definite improvement over current methods.
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