Abstract
The synthesis of the decapeptide H·Ser‐Tyr‐Ser‐Met‐Glu‐His‐Phe‐Arg‐Try‐Gly·OHt) 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(OBu1)‐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‐, ‐OBut), 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 pituitary9,12). 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‐lysine3)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.
Published Version
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