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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
Author(s) -
Schwyzer R.,
Kappeler H.
Publication year - 1961
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19610440723
Subject(s) - chemistry , residue (chemistry) , stereochemistry , amino acid , lysine , protecting group , catalysis , peptide , biochemistry , organic chemistry , alkyl
The 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.