1469-49-4Relevant articles and documents
Modification of the Enantioselectivity of Biocatalytic meso-Desymmetrization for Synthesis of Both Enantiomers of cis-1,2-Disubstituted Cyclohexane by Amidase Engineering
Hu, Hui-Juan,Wang, Qi-Qiang,Wang, De-Xian,Ao, Yu-Fei
supporting information, p. 4538 - 4543 (2021/08/09)
Both enantiomers of cis-1,2-disubstituted cyclohexane have been obtained enantioselectively through engineered amidase-catalyzed desymmetrization of meso carbocyclic 1,2-dicarboxamides under mild condition. Based on the enzyme-substrate binding model sugg
Rhodococcus rhodochrous IFO 15564-mediated hydrolysis of alicyclic nitriles and amides: Stereoselectivity and use for kinetic resolution and asymmetrization
Matoishi, Kaori,Sano, Akio,Imai, Nori,Yamazaki, Takahiro,Yokoyama, Masahiro,Sugai, Takeshi,Ohta, Hiromichi
, p. 1097 - 1102 (2007/10/03)
The stereocourse and the selectivity of the hydrolysis of alicyclic mono- and dinitriles and amides mediated by Rhodococcus rhodochrous IFO · 15564 has been examined. The stereochemistry of the substrates, as well as the nature of substituents and presence of double bonds in alicyclic rings greatly affected the rate of hydrolysis by nitrile hydratase and amidase. The rate difference between enantiomers or enantiotopic groups, in some cases, enabled kinetic resolution or asymmetrization. The highest enantioselectivity of amidase was observed in the hydrolysis of 5-benzoyloxy-3-cyclohexene-1- carboxamide (E>200), and both enantiomers of methyl 5-hydroxy-3-cyclohexene- 1-carboxylate thus became readily available.