Chemistry Letters · 1993 · 27 citations · 8 references
Life SciencesBiochemistryProtein EngineeringDisulfide Bond FormationPeptide Bond ChemistryPeptide ChemistryFmoc ChemistryOne-pot DeprotectionPeptide Bond Cleavage MechanismsPeptide Chain ElongationPeptide Coupling Reagents
Abstract 9-Fluorenylmethyloxycarbonyl (Fmoc) group can be quickly removed with tetrabutylammonium fluoride hydrate (TBAF·xH2O) in the presence of a large excess of phenylmethanethiol or 1-octanethiol. Subsequent oxidation of the thiol with bis(1-methyl-1H-tetrazol-5-yl) disulfide simultaneously inactivated the TBAF and enabled one-pot peptide bond elongation by the Fmoc strategy.
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New coupling reagents in peptide chemistry
Reinhard Knorr, Arnold Trzeciak, Willi Bannwarth et al. · Tetrahedron Letters · 1989 · 986 citations
Louis A. Carpino, B. J. Cohen, K. E. JUN. STEPHENS et al. · The Journal of Organic Chemistry · 1986 · 193 citations