N-Sulfanylethylaminooxybutyramide (SEAoxy): A Crypto-Thioester Compatible with Fmoc Solid-Phase Peptide Synthesis.
An N-sulfanylethylaminooxybutyramide (SEAoxy) has been developed as a novel thioester equivalent for native chemical ligation. SEAoxy peptide was straightforwardly synthesized by conventional Fmoc solid-phase peptide synthesis without a problem. Moreover, SEAoxy peptide could be directly applied to native chemical ligation owing to the intramolecular N-to-S acyl shift that releases the peptide-thioester in situ. This methodology was successfully applied to the synthesis of two bioactive peptides.
Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.
Shugo
S
Tsuda
Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.
Masayoshi
M
Mochizuki
Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.
Ken
K
Sakamoto
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University , Tokushima 770-8505, Japan.
Masaya
M
Denda
Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.
Hideki
H
Nishio
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University , Tokushima 770-8505, Japan.
Akira
A
Otaka
Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.
Taku
T
Yoshiya