TY  - JOUR
AU  - Boyd, Derek R.
AU  - Sharma, Narain D.
AU  - McMurray, Brian
AU  - Haughey, Simon A.
AU  - Allen, Christopher C. R.
AU  - Hamilton, John T. G.
AU  - McRoberts, W. Colin
AU  - O'Ferrall, Rory A. More
AU  - Nikodinović-Runić, Jasmina
AU  - Coulombel, Lydie A.
AU  - O'Connor, Kevin E.
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1238
AB  - Asymmetric heteroatom oxidation of benzo[b]thiophenes to yield the corresponding sulfoxides was catalysed by toluene dioxygenase (TDO), naphthalene dioxygenase (NDO) and styrene monooxygenase (SMO) enzymes present in P. putida mutant and E. coli recombinant whole cells. TDO-catalysed oxidation yielded the relatively unstable benzo[b] thiophene sulfoxide; its dimerization, followed by dehydrogenation, resulted in the isolation of stable tetracyclic sulfoxides as minor products with cis-dihydrodiols being the dominant metabolites. SMO mainly catalysed the formation of enantioenriched benzo[b] thiophene sulfoxide and 2-methyl benzo[b] thiophene sulfoxides which racemized at ambient temperature. The barriers to pyramidal sulfur inversion of 2- and 3-methyl benzo[b] thiophene sulfoxide metabolites, obtained using TDO and NDO as biocatalysts, were found to be ca.: 25-27 kcal mol(-1). The absolute configurations of the benzo[b] thiophene sulfoxides were determined by ECD spectroscopy, X-ray crystallography and stereochemical correlation. A site-directed mutant E. coli strain containing an engineered form of NDO, was found to change the regioselectivity toward preferential oxidation of the thiophene ring rather than the benzene ring.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic and Biomolecular Chemistry
T1  - Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes
VL  - 10
IS  - 4
SP  - 782
EP  - 790
DO  - 10.1039/c1ob06678a
ER  - 

@article{
author = "Boyd, Derek R. and Sharma, Narain D. and McMurray, Brian and Haughey, Simon A. and Allen, Christopher C. R. and Hamilton, John T. G. and McRoberts, W. Colin and O'Ferrall, Rory A. More and Nikodinović-Runić, Jasmina and Coulombel, Lydie A. and O'Connor, Kevin E.",
year = "2012",
abstract = "Asymmetric heteroatom oxidation of benzo[b]thiophenes to yield the corresponding sulfoxides was catalysed by toluene dioxygenase (TDO), naphthalene dioxygenase (NDO) and styrene monooxygenase (SMO) enzymes present in P. putida mutant and E. coli recombinant whole cells. TDO-catalysed oxidation yielded the relatively unstable benzo[b] thiophene sulfoxide; its dimerization, followed by dehydrogenation, resulted in the isolation of stable tetracyclic sulfoxides as minor products with cis-dihydrodiols being the dominant metabolites. SMO mainly catalysed the formation of enantioenriched benzo[b] thiophene sulfoxide and 2-methyl benzo[b] thiophene sulfoxides which racemized at ambient temperature. The barriers to pyramidal sulfur inversion of 2- and 3-methyl benzo[b] thiophene sulfoxide metabolites, obtained using TDO and NDO as biocatalysts, were found to be ca.: 25-27 kcal mol(-1). The absolute configurations of the benzo[b] thiophene sulfoxides were determined by ECD spectroscopy, X-ray crystallography and stereochemical correlation. A site-directed mutant E. coli strain containing an engineered form of NDO, was found to change the regioselectivity toward preferential oxidation of the thiophene ring rather than the benzene ring.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic and Biomolecular Chemistry",
title = "Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes",
volume = "10",
number = "4",
pages = "782-790",
doi = "10.1039/c1ob06678a"
}

Boyd, D. R., Sharma, N. D., McMurray, B., Haughey, S. A., Allen, C. C. R., Hamilton, J. T. G., McRoberts, W. C., O'Ferrall, R. A. M., Nikodinović-Runić, J., Coulombel, L. A.,& O'Connor, K. E.. (2012). Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes. in Organic and Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 10(4), 782-790.
https://doi.org/10.1039/c1ob06678a

Boyd DR, Sharma ND, McMurray B, Haughey SA, Allen CCR, Hamilton JTG, McRoberts WC, O'Ferrall RAM, Nikodinović-Runić J, Coulombel LA, O'Connor KE. Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes. in Organic and Biomolecular Chemistry. 2012;10(4):782-790.
doi:10.1039/c1ob06678a .

Boyd, Derek R., Sharma, Narain D., McMurray, Brian, Haughey, Simon A., Allen, Christopher C. R., Hamilton, John T. G., McRoberts, W. Colin, O'Ferrall, Rory A. More, Nikodinović-Runić, Jasmina, Coulombel, Lydie A., O'Connor, Kevin E., "Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes" in Organic and Biomolecular Chemistry, 10, no. 4 (2012):782-790,
https://doi.org/10.1039/c1ob06678a . .