156467-85-5Relevant articles and documents
3-Nitro-2-pyridinesulfenates as Efficient Solution- and Solid-Phase Disulfide Bond Forming Agents
Taguchi, Akihiro,Kobayashi, Kiyotaka,Kotani, Akira,Muguruma, Kyohei,Kobayashi, Misaki,Fukumoto, Kentarou,Takayama, Kentaro,Hakamata, Hideki,Hayashi, Yoshio
, p. 8262 - 8267 (2017)
In this paper, a new disulfide-forming agent based on the finding that alkoxy 3-nitro-2-pyridinesulfenates (Npys-OR) can oxidize thiol groups is reported. Methyl 3-nitro-2-pyridinesulfenate (Npys-OMe), which is easily prepared from 3-nitro-2-pyridinesulfenyl chloride in a one-step reaction and has a reduction peak potential (Epc) of ?0.541 V versus Ag/AgCl, produces the cyclic nonapeptide oxytocin from its linear form in good yield (92 %) with minimal oligomer formation. Npys-OMe in the solid phase also demonstrated excellent results in oxytocin synthesis. Other disulfide-containing peptides, such as α-human atrial natriuretic peptide and α-conotoxin ImI, were also successfully synthesized. During these syntheses, no side reactions of methionine (Met) and tryptophan (Trp) residues or the S-acetamidomethyl (Acm) protecting group were detected. These results suggested that Npys-OMe or its solid-phase analog provides a new strategy for regioselective disulfide bond formation to assist the synthesis of complex disulfide-rich peptides.
Selective disulfidation reagent using nitrogen-containing compound and method for producing disulfide-containing compound
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Paragraph 30-32, (2020/12/02)
The present invention provides a means capable of selectively introducing a disulfide bond with respect to two free thiol groups located in a molecule of an organic compound such as a peptide, or the like, in a short time by a simple treatment and also by a chemically stable method. A nitrogen-containing compound represented by Chemical Formula 1 below or a salt thereof: The symbols shown in Chemical Formula 1 are the same as defined in the specification.