- One-Pot/Sequential Native Chemical Ligation Using Photocaged Crypto-thioester
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A practical and efficient methodology for the chemical synthesis of peptides/proteins using a one-pot/sequential ligation is described. It features the use of photocleavable S-protection on an N-sulfanylethylaniline moiety. Removal of the S-protecting ligated materials under UV irradiation provides a readily usable mixture for subsequent native chemical ligation.
- Aihara, Keisuke,Yamaoka, Kosuke,Naruse, Naoto,Inokuma, Tsubasa,Shigenaga, Akira,Otaka, Akira
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- Selective disulfidation reagent using nitrogen-containing compound and method for producing disulfide-containing compound
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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.
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Page/Page column 28-30
(2020/12/02)
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- 3-Nitro-2-pyridinesulfenates as Efficient Solution- and Solid-Phase Disulfide Bond Forming Agents
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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.
- Taguchi, Akihiro,Kobayashi, Kiyotaka,Kotani, Akira,Muguruma, Kyohei,Kobayashi, Misaki,Fukumoto, Kentarou,Takayama, Kentaro,Hakamata, Hideki,Hayashi, Yoshio
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supporting information
p. 8262 - 8267
(2017/06/23)
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