Selective disulfidation reagent using nitrogen-containing compound and method for producing disulfide-containing compound
AssigneesTokyo University of Pharmacy & Life Sciences, Kokusan Chemical Co., Ltd.
InventorsYoshio Hayashi, Akihiro Taguchi, Kentaro Fukumoto
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Abstract
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.
Claims30
A nitrogen-containing compound represented by Chemical Formula 1 below or a salt thereof:
- wherein
- W, together with other ring member atoms, forms a nitrogen-containing heterocycle selected from the group consisting of a pyridine ring, a pyrazine ring, an imidazole ring, an oxazole ring, a thiazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a phenanthroline ring, a pteridine ring, and an azocine ring,
- X is —O— or —NH—,
- Y is selected from the group consisting of a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, and a monovalent group derived from a substituted or unsubstituted aliphatic heterocycle having an electron-withdrawing property,
- Z represents a hydrogen atom or an electron-withdrawing substituent present on the nitrogen-containing heterocycle,
- p, q, and r are each independently 0 or 1,
- s represents an integer of 0 to 10,
- L0 and L1 each independently represent a linker having a chemically stable structure,
- Aa and Ab are each independently a group selected from the group consisting of —CH═CH—, —C≡C—, —C(═O)—, —C(═O)—O—, —O—C(═O)—, —O—, C1-C20 oxyalkylene group, C1-C20 alkyleneoxy group, —C(═O)—NH—, —NH—C(═O)—, —NH—C(═O)—NH—, hydrazine, triazole, sulfone, sulfoxide, sulfonic acid ester, sulfonamide, sulfinic acid ester, sulfinamide, piperidine, and dioxane, and
- R is a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C20 alkenyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 cycloalkenyl group, a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, an amino group, a hydroxy group, or a polymer carrier;
- provided that the following compounds (A) to (H) are excluded:
- (A) 3-nitro-2-pyridine sulfinic acid methyl,
- (B) 3-nitro-2-pyridine sulfinic acid ethyl,
- (C) 3-nitro-2-pyridine sulfinic acid N,N-diethylaminoethyl,
- (D) N-(3′-nitro-T-pyridinesulfenyloxy)-5-norbornene-2,3-dicarboxyimide,
- (E) (S)-((tert-butoxycarbonyl)amino)-3-(((3-nitropyridin-2-yl)thio)oxy)propanoic acid,
- (F) (2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-(((3-nitropyridin-2-yl)thio)oxy)butanoic acid,
- (G) 4-((((3-nitropyridin-2-yl)thio)oxy)methyl)benzoic acid, and
- (H) (S)-2-(((3-nitropyridin-2-yl)thio)oxy)-3-phenylpropanoic acid.
Dependencies are inferred from the claim text.