Highly Enantioselective Reduction of α-Methylated Nitroalkenes
Burda E, Reß T, Winkler T, Giese C, Kostrov X, Huber T, Hummel W, Gröger H (2013)
Angewandte Chemie (International ed. in English) 52(35): 9323-9326.
Zeitschriftenaufsatz
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Autor*in
Burda, Edyta;
Reß, TinaUniBi;
Winkler, Till;
Giese, CarolinUniBi;
Kostrov, Xenia;
Huber, Tobias;
Hummel, WernerUniBi;
Gröger, HaraldUniBi
Abstract / Bemerkung
Highly selective: The reduction of α-methyl-substituted nitroalkenes succeeds in a highly enantioselective fashion with an ene reductase from Gluconobacter oxydans. Under optimized reaction conditions the desired nitroalkanes are formed with enantiomeric excesses of up to 95% in these biotransformations.
Erscheinungsjahr
2013
Zeitschriftentitel
Angewandte Chemie (International ed. in English)
Band
52
Ausgabe
35
Seite(n)
9323-9326
ISSN
1433-7851
Page URI
https://pub.uni-bielefeld.de/record/2621189
Zitieren
Burda E, Reß T, Winkler T, et al. Highly Enantioselective Reduction of α-Methylated Nitroalkenes. Angewandte Chemie (International ed. in English). 2013;52(35):9323-9326.
Burda, E., Reß, T., Winkler, T., Giese, C., Kostrov, X., Huber, T., Hummel, W., et al. (2013). Highly Enantioselective Reduction of α-Methylated Nitroalkenes. Angewandte Chemie (International ed. in English), 52(35), 9323-9326. doi:10.1002/anie.201301814
Burda, Edyta, Reß, Tina, Winkler, Till, Giese, Carolin, Kostrov, Xenia, Huber, Tobias, Hummel, Werner, and Gröger, Harald. 2013. “Highly Enantioselective Reduction of α-Methylated Nitroalkenes”. Angewandte Chemie (International ed. in English) 52 (35): 9323-9326.
Burda, E., Reß, T., Winkler, T., Giese, C., Kostrov, X., Huber, T., Hummel, W., and Gröger, H. (2013). Highly Enantioselective Reduction of α-Methylated Nitroalkenes. Angewandte Chemie (International ed. in English) 52, 9323-9326.
Burda, E., et al., 2013. Highly Enantioselective Reduction of α-Methylated Nitroalkenes. Angewandte Chemie (International ed. in English), 52(35), p 9323-9326.
E. Burda, et al., “Highly Enantioselective Reduction of α-Methylated Nitroalkenes”, Angewandte Chemie (International ed. in English), vol. 52, 2013, pp. 9323-9326.
Burda, E., Reß, T., Winkler, T., Giese, C., Kostrov, X., Huber, T., Hummel, W., Gröger, H.: Highly Enantioselective Reduction of α-Methylated Nitroalkenes. Angewandte Chemie (International ed. in English). 52, 9323-9326 (2013).
Burda, Edyta, Reß, Tina, Winkler, Till, Giese, Carolin, Kostrov, Xenia, Huber, Tobias, Hummel, Werner, and Gröger, Harald. “Highly Enantioselective Reduction of α-Methylated Nitroalkenes”. Angewandte Chemie (International ed. in English) 52.35 (2013): 9323-9326.
4 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
Better than Nature: Nicotinamide Biomimetics That Outperform Natural Coenzymes.
Knaus T, Paul CE, Levy CW, de Vries S, Mutti FG, Hollmann F, Scrutton NS., J Am Chem Soc 138(3), 2016
PMID: 26727612
Knaus T, Paul CE, Levy CW, de Vries S, Mutti FG, Hollmann F, Scrutton NS., J Am Chem Soc 138(3), 2016
PMID: 26727612
Systematic methodology for the development of biocatalytic hydrogen-borrowing cascades: application to the synthesis of chiral α-substituted carboxylic acids from α-substituted α,β-unsaturated aldehydes.
Knaus T, Mutti FG, Humphreys LD, Turner NJ, Scrutton NS., Org Biomol Chem 13(1), 2015
PMID: 25372591
Knaus T, Mutti FG, Humphreys LD, Turner NJ, Scrutton NS., Org Biomol Chem 13(1), 2015
PMID: 25372591
Enantioselective organocatalytic reduction of β-trifluoromethyl nitroalkenes: an efficient strategy for the synthesis of chiral β-trifluoromethyl amines.
Massolo E, Benaglia M, Orlandi M, Rossi S, Celentano G., Chemistry 21(9), 2015
PMID: 25573847
Massolo E, Benaglia M, Orlandi M, Rossi S, Celentano G., Chemistry 21(9), 2015
PMID: 25573847
Chemoselective biocatalytic reduction of conjugated nitroalkenes: new application for an Escherichia coli BL21(DE3) expression strain.
Jovanovic P, Jeremic S, Djokic L, Savic V, Radivojevic J, Maslak V, Ivkovic B, Vasiljevic B, Nikodinovic-Runic J., Enzyme Microb Technol 60(), 2014
PMID: 24835095
Jovanovic P, Jeremic S, Djokic L, Savic V, Radivojevic J, Maslak V, Ivkovic B, Vasiljevic B, Nikodinovic-Runic J., Enzyme Microb Technol 60(), 2014
PMID: 24835095
35 References
Daten bereitgestellt von Europe PubMed Central.
Kleemann, 2001
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Barrett, Tetrahedron Lett. 29(), 1988
syn-Selective catalytic asymmetric nitro-Mannich reactions using a heterobimetallic Cu-Sm-Schiff base complex.
Handa S, Gnanadesikan V, Matsunaga S, Shibasaki M., J. Am. Chem. Soc. 129(16), 2007
PMID: 17394322
Handa S, Gnanadesikan V, Matsunaga S, Shibasaki M., J. Am. Chem. Soc. 129(16), 2007
PMID: 17394322
AUTHOR UNKNOWN, 0
Li, J. Chin. Chem. Soc. 49(), 2002
Li, J. Chem. Res. Synop. 3(), 2003
AUTHOR UNKNOWN, 0
Toogood, ChemCatChem 2(), 2010
Asymmetric bioreduction of activated C=C bonds using enoate reductases from the old yellow enzyme family.
Stuermer R, Hauer B, Hall M, Faber K., Curr Opin Chem Biol 11(2), 2007
PMID: 17353140
Stuermer R, Hauer B, Hall M, Faber K., Curr Opin Chem Biol 11(2), 2007
PMID: 17353140
Bougioukou, 2012
AUTHOR UNKNOWN, 0
Sakai, Agric. Biol. Chem. 49(), 1985
Bak, Aust. J. Chem. 49(), 1996
Kawai, Tetrahedron: Asymmetry 12(), 2001
Highly enantioselective reduction of beta,beta-disubstituted aromatic nitroalkenes catalyzed by Clostridium sporogenes.
Fryszkowska A, Fisher K, Gardiner JM, Stephens GM., J. Org. Chem. 73(11), 2008
PMID: 18452336
Fryszkowska A, Fisher K, Gardiner JM, Stephens GM., J. Org. Chem. 73(11), 2008
PMID: 18452336
Korbekandi, Enzyme Microb. Technol. 42(), 2008
A site-saturated mutagenesis study of pentaerythritol tetranitrate reductase reveals that residues 181 and 184 influence ligand binding, stereochemistry and reactivity.
Toogood HS, Fryszkowska A, Hulley M, Sakuma M, Mansell D, Stephens GM, Gardiner JM, Scrutton NS., Chembiochem 12(5), 2011
PMID: 21374779
Toogood HS, Fryszkowska A, Hulley M, Sakuma M, Mansell D, Stephens GM, Gardiner JM, Scrutton NS., Chembiochem 12(5), 2011
PMID: 21374779
Asymmetric bioreduction of alkenes using ene-reductases YersER and KYE1 and effects of organic solvents.
Yanto Y, Winkler CK, Lohr S, Hall M, Faber K, Bommarius AS., Org. Lett. 13(10), 2011
PMID: 21510626
Yanto Y, Winkler CK, Lohr S, Hall M, Faber K, Bommarius AS., Org. Lett. 13(10), 2011
PMID: 21510626
Classen, ChemCatChem 5(), 2013
AUTHOR UNKNOWN, 0
Li, Angew. Chem. 124(), 2012
Highly enantioselective hydrogenation of β,β-disubstituted nitroalkenes.
Li S, Huang K, Cao B, Zhang J, Wu W, Zhang X., Angew. Chem. Int. Ed. Engl. 51(34), 2012
PMID: 22807193
Li S, Huang K, Cao B, Zhang J, Wu W, Zhang X., Angew. Chem. Int. Ed. Engl. 51(34), 2012
PMID: 22807193
Reductive biotransformation of nitroalkenes via nitroso-intermediates to oxazetes catalyzed by xenobiotic reductase A (XenA).
Durchschein K, Fabian WM, Macheroux P, Zangger K, Trimmel G, Faber K., Org. Biomol. Chem. 9(9), 2011
PMID: 21409264
Durchschein K, Fabian WM, Macheroux P, Zangger K, Trimmel G, Faber K., Org. Biomol. Chem. 9(9), 2011
PMID: 21409264
Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans.
Richter N, Groger H, Hummel W., Appl. Microbiol. Biotechnol. 89(1), 2010
PMID: 20717668
Richter N, Groger H, Hummel W., Appl. Microbiol. Biotechnol. 89(1), 2010
PMID: 20717668
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Mueller, Adv. Synth. Catal. 352(), 2010
Crystal structure determination and mutagenesis analysis of the ene reductase NCR.
Reich S, Hoeffken HW, Rosche B, Nestl BM, Hauer B., Chembiochem 13(16), 2012
PMID: 23033175
Reich S, Hoeffken HW, Rosche B, Nestl BM, Hauer B., Chembiochem 13(16), 2012
PMID: 23033175
AUTHOR UNKNOWN, 0
Sakai, Tetrahedron Lett. 39(), 1998
Biochemical characterisation of a NADPH-dependent carbonyl reductase from Neurospora crassa reducing α- and β-keto esters.
Richter N, Hummel W., Enzyme Microb. Technol. 48(6-7), 2011
PMID: 22113019
Richter N, Hummel W., Enzyme Microb. Technol. 48(6-7), 2011
PMID: 22113019
Sakai, Tetrahedron: Asymmetry 15(), 2004
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