K. Inouye, Kunio Watanabe
1977
Citations
0
Influential Citations
3
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
An undecapeptide derivative, Z–Lys(Mhoc)–Pro–Val–Gly–Lys(Mhoc)–Lys(Mhoc)–Arg–Arg–Pro–Val–Lys–(Mhoc)–NHNH2, corresponding to the amino acid sequence 11–21 of corticotropin (ACTH)is synthesized. In the course of the synthesis a key intermediate H–Arg(NO2)–Arg(NO2)–Pro–OH is derived from Z–Arg(NO2)–Arg–(NO2)–Pro–OBzl by the treatment with hydrogen bromide in acetic acid. This procedure eliminates the danger of racemization associated with the use of alkali for saponification. The synthesis is also described of a nonapeptide derivative, Z–Lys(Mhoc)–Pro–Val–Gly–Lys(Mhoc)–Lys(Mhoc)–Arg(NO2)–Arg(NO2)–Pro–OH (amino acid sequence 11–19 of ACTH), in which a new protecting group, 9-methyl-9-fluorenyloxycarbonyl (Mfoc), is utilized for the temporary protection of an α-amino function.