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Epimerization-Free Preparation of C-Terminal Cys Peptide Acid by Fmoc SPPS Using Pseudoproline-Type Protecting Group
Shugo Tsuda1, Shun Masuda1, Taku Yoshiya1
1Peptide Institute, Inc. , 7-2-9 Saito-asagi , Ibaraki-shi , Osaka 567-0085 , Japan.
The Journal of Organic Chemistry
|October 22, 2019
Abstract:
Preparation of C-terminal Cys-containing peptide acid by Fmoc solid-phase peptide synthesis (SPPS) is difficult due to base-mediated epimerization at Cys. In this paper, use of a C-terminal pseudoproline structure and Trt(2-Cl) resin achieved epimerization-free direct preparation of the C-terminal Cys-containing peptide acid by Fmoc SPPS. Additionally, the C-terminal Cys(ΨDmp,Hpro)-containing protected peptide segment was applied to an epimerization-free segment condensation reaction.
