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Report No.

Solid-phase synthesis of cyclic peptides containing p-(tri-n-butyl-stannyl)-phenylalanine residue

Tsukui, Narutaka; Yamada, Keiichi*; Watanabe, Shigeki; Hanaoka, Hirofumi*; Oku, Hiroyuki*; Endo, Keigo*; Ishioka, Noriko; Matsuo, Ichiro*

p-(tri-n-butyl-stannyl)-phenylalanine (Phe(p-Bu$$_{3}$$Sn)) is an useful building blocks for synthesizing radiolabeled pharmaceutics. To best of our knowledge, there are few studies of the synthesis of Phe(p-Bu$$_{3}$$Sn)-containing peptides. In this study, we report solid-phase synthesis of cyclic peptides containing Phe(p-Bu$$_{3}$$Sn) residue, cyclo(Phe(p-Bu$$_{3}$$Sn)-Leu-MeLeu-Val-Leu) (I). Boc-Phe(p-Bu$$_{3}$$Sn)-OH was synthesized from Boc-Phe(p-I)-OMe by treatment with bis(tri-n-butyl)tin and Pd(0) catalyst followed by saponification. The linear peptide containing Phe(p-Bu$$_{3}$$Sn) residue was assembled on Kaiser-oxime resin. On-resin macrocyclization of the linear peptide, however, did not afford the cyclic peptide I. Cross coupling of cyclic peptide containing Phe(p-I) residue, cyclo(Phe(p-I)-Leu-MeLeu-Val-Leu) with bis(tri-n-butyl)tin and Pd(0) catalyst gave the desired peptide, which was confirmed by ESI-MS. In this presentation, we will report the Fmoc-SPPS of the peptide I.



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