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4‐Fluorophenyl 3‐nitro‐2‐pyridinesulfenate as a practical protecting agent for amino acids
Author(s) -
Cui Yan,
Rentier Cédric,
Taguchi Akihiro,
Takayama Kentaro,
Taniguchi Atsuhiko,
Hayashi Yoshio
Publication year - 2018
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.3070
Subject(s) - chemistry , pyridine , nitro , thiol , protecting group , base (topology) , chloride , phenols , reactivity (psychology) , combinatorial chemistry , organic chemistry , medicine , mathematical analysis , alkyl , alternative medicine , mathematics , pathology
We report a new protecting agent ( 1 , Npys‐OPh( p F)) 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.