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Novel coupling of thiols into disulfides, via S-Nitrosothiol intermediates using trichloronitromethane
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093233.pdf
Date
2000
Author
İğdir, A. Çiğdem
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https://hdl.handle.net/11511/2650
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Graduate School of Natural and Applied Sciences, Thesis
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Novel conversion of thiols into disulfides, via S-nitrosothiol intermediates using trichloronitromethane
Demir, Ayhan Sıtkı; Igdir, AC; Mahasneh, AS (1999-10-15)
An efficient oxidative coupling of thiols to give disulfides via thionitrite (S-nitrosothiol) intermediate is described using trichloronitromethane as an efficient reagent in organic solvents and water. Cysteine and glutathione are converted into the corresponding disulfides in water in high yields.
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A new enantioselective synthesis of furan-2-yl amines and amino acids is described, in which the key step is the oxazaborolidine-catalyzed enantioselective reduction of O-benzyl (E)- and (Z)-furan-2-yl ketone oximes to the corresponding chiral amines. The chirality of the furan-2-yl amines is fully controlled by the appropriate choice of the geometrical isomer of the O-benzyl oxime. Oxidation of the furan ring furnished amino acids in high yields.
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Novel enantioselective synthesis of trans-α-(2-carboxycyclo-prop-1- yl)glycines: Conformationally constrained L-glutamate analogues
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D- and L-alpha-(2-carboxycycloprop-1-yl)glycines were synthesized from trans-1,3-di(2-furyl)propenane. Conversion of the double bond to a cyclopropane is followed by-the formation of an oxime ether. Enantioselective reduction of the oxime ether, separation of diastereomers and oxidation of the furane rings gave enantiomerically pure D- and L-CCG I and CCG II. The structure of oxime 7b was determined by X-ray crystal structure analysis. The key step is the oxazaborolidine catalyzed enantioselective conversio...
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A. Ç. İğdir, “Novel coupling of thiols into disulfides, via S-Nitrosothiol intermediates using trichloronitromethane,” Middle East Technical University, 2000.