16051-87-9Relevant articles and documents
MONOHYDROLYSIS OF AN ALIPHATIC DINITRILE COMPOUND BY NITRILASE FROM RHODOCOCCUS RHODOCHROUS K22
Kobayashi, Michihiko,Yanaka, Noriyuki,Nagasawa, Toru,Yamada, Hideaki
, p. 5587 - 5590 (1990)
Nitrilase from Rhodococcus rhodochrous K22 catalyzes the conversion of various aliphatic nitrile derivatives to the corresponding acids.Using this resting cells, 4-cyanobutyric acid was synthesized from glutaronitrile with 100percent molar conversion.
A bioorthogonal raman reporter strategy for SERS detection of glycans on live cells
Lin, Liang,Tian, Xiangdong,Hong, Senlian,Dai, Peng,You, Qiancheng,Wang, Ruyi,Feng, Lianshun,Xie, Can,Tian, Zhong-Qun,Chen, Xing
, p. 7266 - 7271 (2013)
Direct detection of glycans on live cells using surface-enhanced Raman scattering (SERS) has been shown. A bioorthogonal Raman reporter was directly installed onto the monosaccharide analogs. Once metabolically incorporated into cell surface glycans, the Raman reporter was detected using SERS (see picture). Copyright
Unusual differences in the reactivity of glutamic and aspartic acid in oxidative decarboxylation reactions
But, Andrada,Van Der Wijst, Evie,Le N?tre, Jér?me,Wever, Ron,Sanders, Johan P. M.,Bitter, Johannes H.,Scott, Elinor L.
, p. 5178 - 5186 (2017)
Amino acids are potential substrates to replace fossil feedstocks for the synthesis of nitriles via oxidative decarboxylation using vanadium chloroperoxidase (VCPO), H2O2 and bromide. Here the conversion of glutamic acid (Glu) and aspartic acid (Asp) was investigated. It was observed that these two chemically similar amino acids have strikingly different reactivity. In the presence of catalytic amounts of NaBr (0.1 equiv.), Glu was converted with high selectivity to 3-cyanopropanoic acid. In contrast, under the same reaction conditions Asp showed low conversion and selectivity towards the nitrile, 2-cyanoacetic acid (AspCN). It was shown that only by increasing the amount of NaBr present in the reaction mixture (from 0.1 to 2 equiv.), could the conversion of Asp be increased from 15% to 100% and its selectivity towards AspCN from 45% to 80%. This contradicts the theoretical hypothesis that bromide is recycled during the reaction. NaBr concentration was found to have a major influence on reactivity, independent of ionic strength of the solution. NaBr is involved not only in the formation of the reactive Br+ species by VCPO, but also results in the formation of potential intermediates which influences reactivity. It was concluded that the difference in reactivity between Asp and Glu must be due to subtle differences in inter- and intramolecular interactions between the functionalities of the amino acids.
Synthesis of α-aminonitriles using aliphatic nitriles, α-amino acids, and hexacyanoferrate as universally applicable non-toxic cyanide sources
Nauth, Alexander M.,Konrad, Tim,Papadopulu, Zaneta,Vierengel, Nina,Lipp, Benjamin,Opatz, Till
supporting information, p. 4217 - 4223 (2018/09/29)
In cyanation reactions, the cyanide source is often directly added to the reaction mixture, which restricts the choice of conditions. The spatial separation of cyanide release and consumption offers higher flexibility instead. Such a setting was used for the cyanation of iminium ions with a variety of different easy-to-handle HCN sources such as hexacyanoferrate, acetonitrile or α-amino acids. The latter substrates were first converted to their corresponding nitriles through oxidative decarboxylation. While glycine directly furnishes HCN in the oxidation step, the aliphatic nitriles derived from α-substituted amino acids can be further converted into the corresponding cyanohydrins in an oxidative C-H functionalization. Mn(OAc)2 was found to catalyze the efficient release of HCN from these cyanohydrins or from acetone cyanohydrin under acidic conditions and, in combination with the two previous transformations, permits the use of protein biomass as a non-toxic source of HCN.
