- Design, synthesis and evaluation of novel P450 fluorescent probes bearing α-cyanoether
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Four α-cyano-containing ethers based on 2-alkoxy-2-naphthylacetonitriles have been designed as a novel structural class of cytochrome P450 fluorescent probes. Their syntheses, fluorescence properties and evaluation in the fluorogenic assay of cytochrome P
- Zhang, Rong,Kang, Kyung-Don,Shan, Guomin,Hammock, Bruce D.
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- Copper-mediated conversion of alkynes into nitriles via iodotriazoles
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We disclose our studies on a copper-mediated reaction of alkynes with trimethylsilyl azide to afford nitriles, and proposed a reaction mechanism, which involves an iodoalkyne and an iodotriazole as intermediates.
- Kori, Ryosuke,Murakami, Keigo,Nishiyama, Yoshitake,Toma, Tatsuya,Yokoshima, Satoshi
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p. 278 - 280
(2021/03/08)
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- A Sterically Congested α-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters
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The cyanation of acetals and orthoesters by using a sterically congested α-cyanoamine as a cyanating reagent was investigated. The α-cyanoamine effectively facilitated cyanation in the presence of trichlorosilyl triflate to produce a variety of cyanated adducts in excellent yields. Analysis of the reaction mixture by 1H NMR spectroscopy revealed that trichlorosilyl triflate produced an oxocarbenium cation species as an intermediate.
- Kotani, Shunsuke,Sakamoto, Midori,Osakama, Kazuki,Nakajima, Makoto
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supporting information
p. 6606 - 6609
(2015/10/29)
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- Chemo-enzymatic synthesis of enantiomerically pure (R)-2-naphthylmethoxyacetic acid
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Enantiomerically pure (R)-2-naphthylmethoxyacetic acid (2-NMA) was synthesized from 2-naphthaldehyde via an integrated chemo-enzymatic procedure. The one-pot, successive use of SnBr2-TMSCN and AcBr worked effectively to give a racemic cyanohydrin acetate. Lipase from Burkholderia cepacia then mediated the highly enantioselective hydrolysis of the (S)-enantiomer of the racemate, leaving the (R)-acetate with an e.e. of >99.9%. The resulting product of this enzyme-catalyzed hydrolysis, an (S)-cyanohydrin, spontaneously decomposed into naphthaldehyde, the starting material of this synthetic route, which could be recycled. The hydration of nitrile to amide as well as the hydrolysis of the acetate was performed with a microorganism, Rhodococcus rhodochrous, under very mild conditions without any loss of the enantiomeric purity. The amide group was hydrolyzed with nitrosylsulfuric acid, and the product was isolated as an α-hydroxy ester. The α-hydroxyl group was methylated with diazomethane-silica gel and the final task, hydrolysis of the ester, was accomplished under conditions as mild as neutral pH with an esterase from Krebsiella oxytoca to give enantiomerically pure 2-NMA.
- Kimura, Mayumi,Kuboki, Atsuhito,Sugai, Takeshi
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p. 1059 - 1068
(2007/10/03)
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