Journal of Peptide Science
Journal of Peptide Science
5 years ago

4-Fluorophenyl 3-nitro-2-pyridinesulfenate as a practical protecting agent for amino acids

4-Fluorophenyl 3-nitro-2-pyridinesulfenate as a practical protecting agent for amino acids
Akihiro Taguchi, Yoshio Hayashi, Atsuhiko Taniguchi, Kentaro Takayama, Cédric Rentier, Yan Cui
We report a new protecting agent (1, Npys-OPh(pF)) for 3-nitro-2-pyridine (Npy) sulfenylation of amino, hydroxy, and thiol functional groups. Several Npys phenoxides were synthesized from Npys chloride (Npys-Cl) and phenols in the presence of base in 1-step reaction, and their ability for Npy-sulfenylation was evaluated. As a result, 1 was selected as a new Npy-sulfenylation agent with advantages including improved physicochemical stability, more controllable reactivity, and easier handling than the conventional protecting agent Npys-Cl. We developed a new protecting reagent, 4-fluorophenyl 3-nitro-2-pyridinesulfenate, Npys-OPh(pF), for Npy-sulfenylation of amino, hydroxy, or thiol groups. This reagent has advantages including superior physicochemical stability, more controllable reactivity, and easier handling than conventional protecting agent Npys-Cl.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/psc.3070

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