Epimerization-Free Preparation of C-Terminal Cys Peptide Acid by Fmoc SPPS Using Pseudoproline-Type Protecting Group.
J Org Chem, 2020/02/07;85(3):1674-1679.
Tsuda S[1], Masuda S[1], Yoshiya T[1]
Affiliations
PMID: 31631664DOI: 10.1021/acs.joc.9b02344
Impact factor: 4.198
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.
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