138769-96-7Relevant articles and documents
Recombinant chlorobenzene dioxygenase from Pseudomonas sp. P51: A biocatalyst for regioselective oxidation of aromatic nitriles
Yildirim, Selcuk,Franko, Telma T.,Wohlgemuth, Roland,Kohler, Hans-Peter E.,Witholt, Bernard,Schmid, Andreas
, p. 1060 - 1072 (2005)
An efficient biocatalyst was developed for the cis-dihydroxylation of aromatic nitriles. The chlorobenzene dioxygenase (CDO) genes of Pseudomonas sp. strain P51 were cloned under the strict control of the Palk promoter of Pseudomonas putida GPo1. Escherichia coli JM101 cells carrying the resulting plasmid pTEZ30 were used for the biotransformation of benzonitrile in a 2-L stirred tank bioreactor. Use of a stable expression system resulted in an average specific activity and an average volumetric productivity of 1.47 U/g cdw and 120 mg of product/h/L, respectively. The values represent a three-fold increase compared to the results of the similar biotransformations with E. coli JM101 (pTCB144) where the genes of CDO were expressed under the control of lac promoter. The productivity of the cis-dihydroxylation process was limited by product toxicity. Removal of the products at toxic concentrations by means of an external charcoal column resulted in an additional increase in product concentration by 43%. E. coli JM101 (pTEZ30) was further used for the regio- and stereospecific dihydroxylations of various monosubstituted benzonitriles, benzyl cyanide, and cinnamonitrile. Biotransformations resulted in products with 42.9-97.1% enantiomeric excess. Initial enzymatic activities and isolated yields were obtained in the range of 1.7-4.7 U/g cdw and of 3-62%, respectively.
Synthesis of (-)-6-hydroxyshikimic acid from ((5S,6R)-5,6-dihydroxy-1,3-cyclohexadienyl)methanenitrile
Tran, Chuong Hao,Crout, David H.G.,Errington, William,Whited, Gregory M.
, p. 691 - 698 (1996)
A six step synthesis of (-)-6-hydroxyshikimic acid 2 has been developed starting from ((5S,6R)-5,6-dihydroxy-1,3-cyclohexadienyl)methanenitrile 3, produced by biotransformation of cyanobenzene by the enzyme toluene dioxygenase.
Aza and oxo Diels-Alder reactions using cis-cyclohexadienediols of microbial origin: Chemoenzymatic preparation of synthetically valuable heterocyclic scaffolds
Pazos, Mariana,Martínez, Sebastián,Vila, María Agustina,Rodríguez, Paola,Veiga, Nicolás,Seoane, Gustavo,Carrera, Ignacio
, p. 1436 - 1447 (2015/12/09)
Aza and oxo Diels-Alder reactions using enantiopure cis-cyclohexadienediols were studied. These dienediols were obtained from the biotransformation of monosubstituted arenes using bacterial dioxygenases (toluene and benzoate dioxygenases). Ethyl glyoxylate and its N-tosyl imine were used as dienophiles to afford the corresponding hetero Diels-Alder bicyclic adducts with excellent regio- and stereoselectivities. Quantum chemical calculations at the B3LYP/6-31+G(d,p) level of theory were performed to rationalize the observed selectivities especially the stereochemical aspects of the cycloadditions. The synthetic importance of these adducts is highlighted for the preparation of enantiopure 2,2,3,4,5,6-hexasubstituted piperidine and tetrahydropyran from toluene.