Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Research Support, Non-U.S. Gov’t, Biotechnology and Applied Biochemistry called Nitrite-mediated synthesis of chiral epichlorohydrin using halohydrin dehalogenase from Agrobacterium radiobacter AD1, Author is Jin, Huo-Xi; Hu, Zhong-Ce; Liu, Zhi-Qiang; Zheng, Yu-Guo, which mentions a compound: 60827-45-4, SMILESS is OC[C@H](O)CCl, Molecular C3H7ClO2, Recommanded Product: 60827-45-4.
In the current study, the haloalc. dehalogenase HheC gene from Agrobacterium radiobacter AD1 was synthesized and expressed in Escherichia coli. After purification using Ni-nitrilotriacetic acid affinity chromatog., HheC was used in the synthesis of chiral epichlorohydrin in the presence of NO2-. The optimal pH, temperature, and NO2- concentration for enantioselectivity are 5.0, 37°C, and 60 mM, resp. The maximum velocity and Michaelis constant values for (S)-epichlorohydrin are 714.3 μmol min-1 mg-1 and 17.2 mM, resp., whereas those for (R)-epichlorohydrin are 166.8 μmol min-1 mg-1 and 29.0 mM, resp. Under optimal conditions, (R)-epichlorohydrin with 99% enantiomeric excess was obtained after an 18 Min reaction; the yield reached 41%, which is the highest amount obtained for chiral epichlorohydrin synthesis using haloalc. dehalogenase. In addition, (R)-epichlorohydrin with 99% enantiomeric excess was successfully obtained from 1,3-dichloro-2-propanol by the ring opening of racemic epichlorohydrin in the presence of NO2- after the ring closure of 1,3-dichloro-2-propanol with HheC. To the best of our knowledge, the current study is the first report on the kinetic resolution of epichlorohydrin with NO2- and synthesis of chiral epichlorohydrin with 99% enantiomeric excess from 1,3-dichloro-2-propanol by combining ring closure of 1,3-dichloro-2-propanol and ring opening of racemic epichlorohydrin.
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Reference:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com