-
1
-
-
84920913613
-
Improving and repurposing biocatalysts via directed evolution
-
Denard, C.A., Ren, H., Zhao, H., Improving and repurposing biocatalysts via directed evolution. Curr Opin Chem Biol 25 (2015), 55–64.
-
(2015)
Curr Opin Chem Biol
, vol.25
, pp. 55-64
-
-
Denard, C.A.1
Ren, H.2
Zhao, H.3
-
2
-
-
84920872755
-
Enzyme engineering in the context of novel pathways and products
-
Otte, K.B., Hauer, B., Enzyme engineering in the context of novel pathways and products. Curr Opin Biotechnol 35 (2015), 16–22.
-
(2015)
Curr Opin Biotechnol
, vol.35
, pp. 16-22
-
-
Otte, K.B.1
Hauer, B.2
-
3
-
-
84947447600
-
Chemomimetic biocatalysis: exploiting the synthetic potential of cofactor-dependent enzymes to create new catalysts
-
Prier, C.K., Arnold, F.H., Chemomimetic biocatalysis: exploiting the synthetic potential of cofactor-dependent enzymes to create new catalysts. J Am Chem Soc 137 (2015), 13992–14006.
-
(2015)
J Am Chem Soc
, vol.137
, pp. 13992-14006
-
-
Prier, C.K.1
Arnold, F.H.2
-
4
-
-
84977900288
-
Genetic optimization of metalloenzymes: enhancing enzymes for non-natural reactions
-
Hyster, T.K., Ward, T.R., Genetic optimization of metalloenzymes: enhancing enzymes for non-natural reactions. Angew Chem Int Ed Engl 55 (2016), 7344–7357.
-
(2016)
Angew Chem Int Ed Engl
, vol.55
, pp. 7344-7357
-
-
Hyster, T.K.1
Ward, T.R.2
-
5
-
-
84961382184
-
Expanding the enzyme universe: accessing non-natural reactions by mechanism-guided directed evolution
-
Renata, H., Wang, Z.J., Arnold, F.H., Expanding the enzyme universe: accessing non-natural reactions by mechanism-guided directed evolution. Angew Chem Int Ed Engl 54 (2015), 3351–3367.
-
(2015)
Angew Chem Int Ed Engl
, vol.54
, pp. 3351-3367
-
-
Renata, H.1
Wang, Z.J.2
Arnold, F.H.3
-
6
-
-
84872495336
-
Olefin cyclopropanation via carbene transfer catalyzed by engineered cytochrome P450 enzymes
-
Coelho, P.S., Brustad, E.M., Kannan, A., Arnold, F.H., Olefin cyclopropanation via carbene transfer catalyzed by engineered cytochrome P450 enzymes. Science 339 (2013), 307–310.
-
(2013)
Science
, vol.339
, pp. 307-310
-
-
Coelho, P.S.1
Brustad, E.M.2
Kannan, A.3
Arnold, F.H.4
-
7
-
-
84880921220
-
A serine-substituted P450 catalyzes highly efficient carbene transfer to olefins in vivo
-
Coelho, P.S., Wang, Z.J., Ener, M.E., Baril, S.A., Kannan, A., Arnold, F.H., Brustad, E.M., A serine-substituted P450 catalyzes highly efficient carbene transfer to olefins in vivo. Nat Chem Biol 9 (2013), 485–487.
-
(2013)
Nat Chem Biol
, vol.9
, pp. 485-487
-
-
Coelho, P.S.1
Wang, Z.J.2
Ener, M.E.3
Baril, S.A.4
Kannan, A.5
Arnold, F.H.6
Brustad, E.M.7
-
8
-
-
84903168457
-
Improved cyclopropanation activity of histidine-ligated cytochrome P450 enables the enantioselective formal synthesis of levomilnacipran
-
Wang, Z.J., Renata, H., Peck, N.E., Farwell, C.C., Coelho, P.S., Arnold, F.H., Improved cyclopropanation activity of histidine-ligated cytochrome P450 enables the enantioselective formal synthesis of levomilnacipran. Angew Chem Int Ed Engl 53 (2014), 6810–6813.
-
(2014)
Angew Chem Int Ed Engl
, vol.53
, pp. 6810-6813
-
-
Wang, Z.J.1
Renata, H.2
Peck, N.E.3
Farwell, C.C.4
Coelho, P.S.5
Arnold, F.H.6
-
9
-
-
84891459977
-
Cytochrome P450-catalyzed insertion of carbenoids into N–H bonds
-
Wang, Z.J., Peck, N.E., Renata, H., Arnold, F.H., Cytochrome P450-catalyzed insertion of carbenoids into N–H bonds. Chem Sci 5 (2014), 598–601.
-
(2014)
Chem Sci
, vol.5
, pp. 598-601
-
-
Wang, Z.J.1
Peck, N.E.2
Renata, H.3
Arnold, F.H.4
-
10
-
-
84924242424
-
Enzymatic C(sp)-H amination: P450-catalyzed conversion of carbonazidates into oxazolidinones
-
Singh, R., Kolev, J.N., Sutera, P.A., Fasan, R., Enzymatic C(sp)-H amination: P450-catalyzed conversion of carbonazidates into oxazolidinones. ACS Catal 5 (2015), 1685–1691.
-
(2015)
ACS Catal
, vol.5
, pp. 1685-1691
-
-
Singh, R.1
Kolev, J.N.2
Sutera, P.A.3
Fasan, R.4
-
11
-
-
84893822655
-
P450-catalyzed intramolecular C–H amination with arylsulfonyl azide substrates
-
Singh, R., Bordeaux, M., Fasan, R., P450-catalyzed intramolecular C–H amination with arylsulfonyl azide substrates. ACS Catal 4 (2014), 546–552.
-
(2014)
ACS Catal
, vol.4
, pp. 546-552
-
-
Singh, R.1
Bordeaux, M.2
Fasan, R.3
-
12
-
-
84902664223
-
Enantioselective imidation of sulfides via enzyme-catalyzed intermolecular nitrogen-atom transfer
-
Farwell, C.C., McIntosh, J.A., Hyster, T.K., Wang, Z.J., Arnold, F.H., Enantioselective imidation of sulfides via enzyme-catalyzed intermolecular nitrogen-atom transfer. J Am Chem Soc 136 (2014), 8766–8771.
-
(2014)
J Am Chem Soc
, vol.136
, pp. 8766-8771
-
-
Farwell, C.C.1
McIntosh, J.A.2
Hyster, T.K.3
Wang, Z.J.4
Arnold, F.H.5
-
13
-
-
84947430009
-
Enantioselective enzyme-catalyzed aziridination enabled by active-site evolution of a cytochrome P450
-
Farwell, C.C., Zhang, R.K., McIntosh, J.A., Hyster, T.K., Arnold, F.H., Enantioselective enzyme-catalyzed aziridination enabled by active-site evolution of a cytochrome P450. ACS Cent Sci 1 (2015), 89–93.
-
(2015)
ACS Cent Sci
, vol.1
, pp. 89-93
-
-
Farwell, C.C.1
Zhang, R.K.2
McIntosh, J.A.3
Hyster, T.K.4
Arnold, F.H.5
-
14
-
-
84883040115
-
Enantioselective intramolecular C–H amination catalyzed by engineered cytochrome P450 enzymes in vitro and in vivo
-
McIntosh, J.A., Coelho, P.S., Farwell, C.C., Wang, Z.J., Lewis, J.C., Brown, T.R., Arnold, F.H., Enantioselective intramolecular C–H amination catalyzed by engineered cytochrome P450 enzymes in vitro and in vivo. Angew Chem Int Ed Engl 52 (2013), 9309–9312.
-
(2013)
Angew Chem Int Ed Engl
, vol.52
, pp. 9309-9312
-
-
McIntosh, J.A.1
Coelho, P.S.2
Farwell, C.C.3
Wang, Z.J.4
Lewis, J.C.5
Brown, T.R.6
Arnold, F.H.7
-
15
-
-
84908616475
-
Enzyme-controlled nitrogen-atom transfer enables regiodivergent C–H amination
-
Hyster, T.K., Farwell, C.C., Buller, A.R., McIntosh, J.A., Arnold, F.H., Enzyme-controlled nitrogen-atom transfer enables regiodivergent C–H amination. J Am Chem Soc 136 (2014), 15505–15508.
-
(2014)
J Am Chem Soc
, vol.136
, pp. 15505-15508
-
-
Hyster, T.K.1
Farwell, C.C.2
Buller, A.R.3
McIntosh, J.A.4
Arnold, F.H.5
-
16
-
-
84922065193
-
Highly diastereoselective and enantioselective olefin cyclopropanation using engineered myoglobin-based catalysts
-
Bordeaux, M., Tyagi, V., Fasan, R., Highly diastereoselective and enantioselective olefin cyclopropanation using engineered myoglobin-based catalysts. Angew Chem Int Ed Engl 54 (2015), 1744–1748.
-
(2015)
Angew Chem Int Ed Engl
, vol.54
, pp. 1744-1748
-
-
Bordeaux, M.1
Tyagi, V.2
Fasan, R.3
-
17
-
-
84924229223
-
Myoglobin-catalyzed intermolecular carbene N–H insertion with arylamine substrates
-
Sreenilayam, G., Fasan, R., Myoglobin-catalyzed intermolecular carbene N–H insertion with arylamine substrates. Chem Commun (Camb) 51 (2015), 1532–1534.
-
(2015)
Chem Commun (Camb)
, vol.51
, pp. 1532-1534
-
-
Sreenilayam, G.1
Fasan, R.2
-
18
-
-
84925002902
-
Intermolecular carbene S–H insertion catalysed by engineered myoglobin-based catalysts
-
Tyagi, V., Bonn, R.B., Fasan, R., Intermolecular carbene S–H insertion catalysed by engineered myoglobin-based catalysts. Chem Sci 6 (2015), 2488–2494.
-
(2015)
Chem Sci
, vol.6
, pp. 2488-2494
-
-
Tyagi, V.1
Bonn, R.B.2
Fasan, R.3
-
19
-
-
84908646955
-
Intramolecular C(sp(3))H amination of arylsulfonyl azides with engineered and artificial myoglobin-based catalysts
-
Bordeaux, M., Singh, R., Fasan, R., Intramolecular C(sp(3))H amination of arylsulfonyl azides with engineered and artificial myoglobin-based catalysts. Bioorg Med Chem 22 (2014), 5697–5704.
-
(2014)
Bioorg Med Chem
, vol.22
, pp. 5697-5704
-
-
Bordeaux, M.1
Singh, R.2
Fasan, R.3
-
20
-
-
84988910889
-
Non-natural carbenoid and nitrenoid insertion reactions catalyzed by heme proteins
-
Gober, J.G., Brustad, E.M., Non-natural carbenoid and nitrenoid insertion reactions catalyzed by heme proteins. Curr Opin Chem Biol 35 (2016), 124–132.
-
(2016)
Curr Opin Chem Biol
, vol.35
, pp. 124-132
-
-
Gober, J.G.1
Brustad, E.M.2
-
21
-
-
84949190783
-
The nature of chemical innovation: new enzymes by evolution
-
Arnold, F.H., The nature of chemical innovation: new enzymes by evolution. Q Rev Biophys 48 (2015), 404–410.
-
(2015)
Q Rev Biophys
, vol.48
, pp. 404-410
-
-
Arnold, F.H.1
-
22
-
-
84997080010
-
Directed evolution of cytochrome c for carbon-silicon bond formation: bringing silicon to life
-
First biocatalytic carbon-silicon bond formation, catalyzed by engineered variants of cytochrome c from Rhodothermus marinus. The engineered catalyst shows excellent chemoselectivities and enantioselectivities and exceeds the turnover of existing synthetic catalysts for carbon-silicon bond formation by 80-fold.
-
Kan, S.B., Lewis, R.D., Chen, K., Arnold, F.H., Directed evolution of cytochrome c for carbon-silicon bond formation: bringing silicon to life. Science 354 (2016), 1048–1051 First biocatalytic carbon-silicon bond formation, catalyzed by engineered variants of cytochrome c from Rhodothermus marinus. The engineered catalyst shows excellent chemoselectivities and enantioselectivities and exceeds the turnover of existing synthetic catalysts for carbon-silicon bond formation by 80-fold.
-
(2016)
Science
, vol.354
, pp. 1048-1051
-
-
Kan, S.B.1
Lewis, R.D.2
Chen, K.3
Arnold, F.H.4
-
23
-
-
84991204363
-
Biocatalytic Synthesis of allylic and allenyl sulfides through a myoglobin-catalyzed Doyle–Kirmse reaction
-
Myoglobin variants catalyze [2,3]-sigmatropic rearrangements of allylic and propargylic sulfides in the presence of α-diazoester reagents. This transformation was applied to a range of sulfide substrates with high conversion (up to 99%) and up to 71% enantioselectivity.
-
Tyagi, V., Sreenilayam, G., Bajaj, P., Tinoco, A., Fasan, R., Biocatalytic Synthesis of allylic and allenyl sulfides through a myoglobin-catalyzed Doyle–Kirmse reaction. Angew Chem Int Ed Engl 55 (2016), 13562–13566 Myoglobin variants catalyze [2,3]-sigmatropic rearrangements of allylic and propargylic sulfides in the presence of α-diazoester reagents. This transformation was applied to a range of sulfide substrates with high conversion (up to 99%) and up to 71% enantioselectivity.
-
(2016)
Angew Chem Int Ed Engl
, vol.55
, pp. 13562-13566
-
-
Tyagi, V.1
Sreenilayam, G.2
Bajaj, P.3
Tinoco, A.4
Fasan, R.5
-
24
-
-
84954348262
-
Myoglobin-catalyzed olefination of aldehydes
-
Tyagi, V., Fasan, R., Myoglobin-catalyzed olefination of aldehydes. Angew Chem Int Ed Engl 55 (2016), 2512–2516.
-
(2016)
Angew Chem Int Ed Engl
, vol.55
, pp. 2512-2516
-
-
Tyagi, V.1
Fasan, R.2
-
25
-
-
84981762933
-
Enzyme-catalyzed carbonyl olefination by the E. coli protein YfeX in the absence of phosphines
-
Weissenborn, M.J.L., Sebastian, A., Borlinghaus, N., Kuhn, M., Kummer, S., Rami, F., Plietker, B., Hauer, B., Enzyme-catalyzed carbonyl olefination by the E. coli protein YfeX in the absence of phosphines. ChemCatChem 8 (2017), 1636–1640.
-
(2017)
ChemCatChem
, vol.8
, pp. 1636-1640
-
-
Weissenborn, M.J.L.1
Sebastian, A.2
Borlinghaus, N.3
Kuhn, M.4
Kummer, S.5
Rami, F.6
Plietker, B.7
Hauer, B.8
-
26
-
-
85023627759
-
P450-mediated non-natural cyclopropanation of dehydroalanine-containing thiopeptides
-
Gober, J.G., Ghodge, S.V., Bogart, J.W., Wever, W.J., Watkins, R.R., Brustad, E.M., Bowers, A.A., P450-mediated non-natural cyclopropanation of dehydroalanine-containing thiopeptides. ACS Chem Biol, 2017, 10.1021/acschembio.7b00358.
-
(2017)
ACS Chem Biol
-
-
Gober, J.G.1
Ghodge, S.V.2
Bogart, J.W.3
Wever, W.J.4
Watkins, R.R.5
Brustad, E.M.6
Bowers, A.A.7
-
27
-
-
84959431926
-
Mutating a Highly Conserved Residue In Diverse Cytochrome P450s facilitates diastereoselective olefin cyclopropanation
-
Interesting report showing the transferability of the known activating T268A mutation across different P450 enzymes to yield improved cyclopropanation catalysts with diverse diastereoselectivities and enantioselectivities.
-
Gober, J.G., Rydeen, A.E., Gibson-O'Grady, E.J., Leuthaeuser, J.B., Fetrow, J.S., Brustad, E.M., Mutating a Highly Conserved Residue In Diverse Cytochrome P450s facilitates diastereoselective olefin cyclopropanation. ChemBioChem 17 (2016), 394–397 Interesting report showing the transferability of the known activating T268A mutation across different P450 enzymes to yield improved cyclopropanation catalysts with diverse diastereoselectivities and enantioselectivities.
-
(2016)
ChemBioChem
, vol.17
, pp. 394-397
-
-
Gober, J.G.1
Rydeen, A.E.2
Gibson-O'Grady, E.J.3
Leuthaeuser, J.B.4
Fetrow, J.S.5
Brustad, E.M.6
-
28
-
-
85018527313
-
Highly diastereo-selectivities and enantioselective synthesis of trifluoromethyl-substituted cyclopropanes via myoglobin-catalyzed transfer of trifluoromethylcarbene
-
2 with myoglobin-catalyzed cyclopropanation to afford chiral trifluoromethyl-substituted cyclopropanes.
-
2 with myoglobin-catalyzed cyclopropanation to afford chiral trifluoromethyl-substituted cyclopropanes.
-
(2017)
J Am Chem Soc
, vol.139
, pp. 5293-5296
-
-
Tinoco, A.1
Steck, V.2
Tyagi, V.3
Fasan, R.4
-
29
-
-
85010791269
-
Selective C–H bond functionalization using repurposed or artificial metalloenzymes
-
Upp, D.M., Lewis, J.C., Selective C–H bond functionalization using repurposed or artificial metalloenzymes. Curr Opin Chem Biol 37 (2017), 48–55.
-
(2017)
Curr Opin Chem Biol
, vol.37
, pp. 48-55
-
-
Upp, D.M.1
Lewis, J.C.2
-
30
-
-
84989260406
-
An evolved orthogonal enzyme/cofactor pair
-
Reynolds, E.W., McHenry, M.W., Cannac, F., Gober, J.G., Snow, C.D., Brustad, E.M., An evolved orthogonal enzyme/cofactor pair. J Am Chem Soc 138 (2016), 12451–12458.
-
(2016)
J Am Chem Soc
, vol.138
, pp. 12451-12458
-
-
Reynolds, E.W.1
McHenry, M.W.2
Cannac, F.3
Gober, J.G.4
Snow, C.D.5
Brustad, E.M.6
-
31
-
-
85019500971
-
Metal substitution modulates the reactivity and extends the reaction scope of myoglobin carbene transfer catalysts
-
Sreenilayam, G., Moore, E.J., Steck, V., Fasan, R., Metal substitution modulates the reactivity and extends the reaction scope of myoglobin carbene transfer catalysts. Adv Synth Catal 359 (2017), 2076–2089.
-
(2017)
Adv Synth Catal
, vol.359
, pp. 2076-2089
-
-
Sreenilayam, G.1
Moore, E.J.2
Steck, V.3
Fasan, R.4
-
32
-
-
84990842428
-
An artificial metalloenzyme with the kinetics of native enzymes
-
Replacement of the heme cofactor with an Ir-porphyrin in P450 CYP119 delivers a biocatalyst capable of catalyzing intra-molecular and intermolecular carbene C–H insertions with up to 35,000 turnovers.
-
Dydio, P., Key, H.M., Nazarenko, A., Rha, J.Y., Seyedkazemi, V., Clark, D.S., Hartwig, J.F., An artificial metalloenzyme with the kinetics of native enzymes. Science 354 (2016), 102–106 Replacement of the heme cofactor with an Ir-porphyrin in P450 CYP119 delivers a biocatalyst capable of catalyzing intra-molecular and intermolecular carbene C–H insertions with up to 35,000 turnovers.
-
(2016)
Science
, vol.354
, pp. 102-106
-
-
Dydio, P.1
Key, H.M.2
Nazarenko, A.3
Rha, J.Y.4
Seyedkazemi, V.5
Clark, D.S.6
Hartwig, J.F.7
-
33
-
-
84975764159
-
Abiological catalysis by artificial haem proteins containing noble metals in place of iron
-
Key, H.M., Dydio, P., Clark, D.S., Hartwig, J.F., Abiological catalysis by artificial haem proteins containing noble metals in place of iron. Nature 534 (2016), 534–537.
-
(2016)
Nature
, vol.534
, pp. 534-537
-
-
Key, H.M.1
Dydio, P.2
Clark, D.S.3
Hartwig, J.F.4
-
34
-
-
85021420663
-
Beyond iron: iridium-containing P450 enzymes for selective cyclopropanations of structurally diverse alkenes
-
Key, H.M., Dydio, P., Liu, Z., Rha, J.Y., Nazarenko, A., Seyedkazemi, V., Clark, D.S., Hartwig, J.F., Beyond iron: iridium-containing P450 enzymes for selective cyclopropanations of structurally diverse alkenes. ACS Cent Sci 3 (2017), 302–308.
-
(2017)
ACS Cent Sci
, vol.3
, pp. 302-308
-
-
Key, H.M.1
Dydio, P.2
Liu, Z.3
Rha, J.Y.4
Nazarenko, A.5
Seyedkazemi, V.6
Clark, D.S.7
Hartwig, J.F.8
-
35
-
-
33845379095
-
Functionalized nitrogen atom transfer catalyzed by cytochrome P-450
-
Svastits, E., Dawson, J., Breslow, R., Gellman, S., Functionalized nitrogen atom transfer catalyzed by cytochrome P-450. J Am Chem Soc 107 (1985), 6427–6428.
-
(1985)
J Am Chem Soc
, vol.107
, pp. 6427-6428
-
-
Svastits, E.1
Dawson, J.2
Breslow, R.3
Gellman, S.4
-
36
-
-
84960516987
-
Asymmetric enzymatic synthesis of allylic amines: a sigmatropic rearrangement strategy
-
A substrate walk approach was applied to engineer cytochrome P411 variants catalyzing sulfimidation/sigmatropic rearrangement reactions to access allylic amines.
-
Prier, C.K., Hyster, T.K., Farwell, C.C., Huang, A., Arnold, F.H., Asymmetric enzymatic synthesis of allylic amines: a sigmatropic rearrangement strategy. Angew Chem Int Ed Engl 55 (2016), 4711–4715 A substrate walk approach was applied to engineer cytochrome P411 variants catalyzing sulfimidation/sigmatropic rearrangement reactions to access allylic amines.
-
(2016)
Angew Chem Int Ed Engl
, vol.55
, pp. 4711-4715
-
-
Prier, C.K.1
Hyster, T.K.2
Farwell, C.C.3
Huang, A.4
Arnold, F.H.5
-
37
-
-
84951201229
-
Efficient conversion of primary azides to aldehydes catalyzed by active site variants of myoglobin
-
Myoglobin variants catalyze oxidative deamination of primary azides to give aldehydes, providing a biocatalytic alternative to conventional aldehyde synthesis protocols based on alcohol oxidation with stoichiometric oxidizing reagents.
-
Giovani, S., Singh, R., Fasan, R., Efficient conversion of primary azides to aldehydes catalyzed by active site variants of myoglobin. Chem Sci 7 (2016), 234–239 Myoglobin variants catalyze oxidative deamination of primary azides to give aldehydes, providing a biocatalytic alternative to conventional aldehyde synthesis protocols based on alcohol oxidation with stoichiometric oxidizing reagents.
-
(2016)
Chem Sci
, vol.7
, pp. 234-239
-
-
Giovani, S.1
Singh, R.2
Fasan, R.3
-
38
-
-
84983349075
-
Aldehyde and ketone synthesis by P450-catalyzed oxidative deamination of alkyl azides
-
Giovani, S., Alwaseem, H., Fasan, R., Aldehyde and ketone synthesis by P450-catalyzed oxidative deamination of alkyl azides. ChemCatChem 8 (2016), 2609–2613.
-
(2016)
ChemCatChem
, vol.8
, pp. 2609-2613
-
-
Giovani, S.1
Alwaseem, H.2
Fasan, R.3
-
39
-
-
84958772431
-
Toluene dioxygenase-catalysed oxidation of benzyl azide to benzonitrile: mechanistic insights for an unprecedented enzymatic transformation
-
Vila, M.A., Pazos, M., Iglesias, C., Veiga, N., Seoane, G., Carrera, I., Toluene dioxygenase-catalysed oxidation of benzyl azide to benzonitrile: mechanistic insights for an unprecedented enzymatic transformation. ChemBioChem 17 (2016), 291–295.
-
(2016)
ChemBioChem
, vol.17
, pp. 291-295
-
-
Vila, M.A.1
Pazos, M.2
Iglesias, C.3
Veiga, N.4
Seoane, G.5
Carrera, I.6
-
40
-
-
84990872382
-
Synthesis of imidazolidin-4-ones via a cytochrome P450-catalyzed intramolecular C–H amination
-
Ren, X., O'Hanlon, J., Morris, M., Robertson, J., Wong, L., Synthesis of imidazolidin-4-ones via a cytochrome P450-catalyzed intramolecular C–H amination. ACS Catal 6 (2016), 6833–6837.
-
(2016)
ACS Catal
, vol.6
, pp. 6833-6837
-
-
Ren, X.1
O'Hanlon, J.2
Morris, M.3
Robertson, J.4
Wong, L.5
-
41
-
-
85021258513
-
Enantioselective, intermolecular benzylic C–H amination catalysed by an engineered iron-haem enzyme
-
Directed evolution of a ‘P411’ variant delivered an enzyme catalyzing amination of benzylic C-H bonds with up to 1300 TTN and high enantioselectivity. While C–H amination typically requires precious metals in small-molecule catalysts, this work showcases new iron heme reactivity achieved by engineering the protein.
-
Prier, C.K., Zhang, R.K., Buller, A.R., Brinkmann-Chen, S., Arnold, F.H., Enantioselective, intermolecular benzylic C–H amination catalysed by an engineered iron-haem enzyme. Nat Chem 9 (2017), 629–634 Directed evolution of a ‘P411’ variant delivered an enzyme catalyzing amination of benzylic C-H bonds with up to 1300 TTN and high enantioselectivity. While C–H amination typically requires precious metals in small-molecule catalysts, this work showcases new iron heme reactivity achieved by engineering the protein.
-
(2017)
Nat Chem
, vol.9
, pp. 629-634
-
-
Prier, C.K.1
Zhang, R.K.2
Buller, A.R.3
Brinkmann-Chen, S.4
Arnold, F.H.5
-
42
-
-
85005808040
-
Gram-scale synthesis of chiral cyclopropane-containing drugs and drug precursors with engineered myoglobin catalysts featuring complementary stereoselectivity
-
Myoglobin variants were engineered to deliver trans-(1R,2R) cyclopropanes, complementing existing trans-(1S,2S)-selective variants. The stereodivergent myoglobins were used to synthesize four drug precursors at gram scale with high diastereoselectivity and enantioselectivity.
-
Bajaj, P., Sreenilayam, G., Tyagi, V., Fasan, R., Gram-scale synthesis of chiral cyclopropane-containing drugs and drug precursors with engineered myoglobin catalysts featuring complementary stereoselectivity. Angew Chem Int Ed Engl 55 (2016), 16110–16114 Myoglobin variants were engineered to deliver trans-(1R,2R) cyclopropanes, complementing existing trans-(1S,2S)-selective variants. The stereodivergent myoglobins were used to synthesize four drug precursors at gram scale with high diastereoselectivity and enantioselectivity.
-
(2016)
Angew Chem Int Ed Engl
, vol.55
, pp. 16110-16114
-
-
Bajaj, P.1
Sreenilayam, G.2
Tyagi, V.3
Fasan, R.4
-
43
-
-
85013217157
-
Highly stereoselective biocatalytic synthesis of key cyclopropane intermediate to ticagrelor
-
Hernandez, K.E., Renata, H., Lewis, R.D., Kan, S.B.J., Zhang, C., Forte, J., Rozzell, D., McIntosh, J.A., Arnold, F.H., Highly stereoselective biocatalytic synthesis of key cyclopropane intermediate to ticagrelor. ACS Catal 6 (2016), 7810–7813.
-
(2016)
ACS Catal
, vol.6
, pp. 7810-7813
-
-
Hernandez, K.E.1
Renata, H.2
Lewis, R.D.3
Kan, S.B.J.4
Zhang, C.5
Forte, J.6
Rozzell, D.7
McIntosh, J.A.8
Arnold, F.H.9
-
44
-
-
84989221063
-
Identification of mechanism-based inactivation in P450-catalyzed cyclopropanation facilitates engineering of improved enzymes
-
A mass-spectrometric approach was use to reveal mechanism-based inactivation processes affecting P450-based cyclopropanation catalysts. Site-directed mutagenesis of two nucleophilic residues prone to alkylation resulted in a P450 variant with >2-fold higher activity.
-
Renata, H., Lewis, R.D., Sweredoski, M.J., Moradian, A., Hess, S., Wang, Z.J., Arnold, F.H., Identification of mechanism-based inactivation in P450-catalyzed cyclopropanation facilitates engineering of improved enzymes. J Am Chem Soc 138 (2016), 12527–12533 A mass-spectrometric approach was use to reveal mechanism-based inactivation processes affecting P450-based cyclopropanation catalysts. Site-directed mutagenesis of two nucleophilic residues prone to alkylation resulted in a P450 variant with >2-fold higher activity.
-
(2016)
J Am Chem Soc
, vol.138
, pp. 12527-12533
-
-
Renata, H.1
Lewis, R.D.2
Sweredoski, M.J.3
Moradian, A.4
Hess, S.5
Wang, Z.J.6
Arnold, F.H.7
-
45
-
-
85011928579
-
Chemoselective, enzymatic C–H bond amination catalyzed by a cytochrome P450 containing an Ir(Me)-PIX cofactor
-
Dydio, P., Key, H.M., Hayashi, H., Clark, D.S., Hartwig, J.F., Chemoselective, enzymatic C–H bond amination catalyzed by a cytochrome P450 containing an Ir(Me)-PIX cofactor. J Am Chem Soc 139 (2017), 1750–1753.
-
(2017)
J Am Chem Soc
, vol.139
, pp. 1750-1753
-
-
Dydio, P.1
Key, H.M.2
Hayashi, H.3
Clark, D.S.4
Hartwig, J.F.5
-
46
-
-
77955823775
-
Heme proteins – diversity in structural characteristics, function, and folding
-
Smith, L.J., Kahraman, A., Thornton, J.M., Heme proteins – diversity in structural characteristics, function, and folding. Proteins 78 (2010), 2349–2368.
-
(2010)
Proteins
, vol.78
, pp. 2349-2368
-
-
Smith, L.J.1
Kahraman, A.2
Thornton, J.M.3
-
47
-
-
84898000543
-
Heme enzyme structure and function
-
Poulos, T.L., Heme enzyme structure and function. Chem Rev 114 (2014), 3919–3962.
-
(2014)
Chem Rev
, vol.114
, pp. 3919-3962
-
-
Poulos, T.L.1
-
48
-
-
84921037626
-
Synthetic biology for the directed evolution of protein biocatalysts: navigating sequence space intelligently
-
Currin, A., Swainston, N., Day, P.J., Kell, D.B., Synthetic biology for the directed evolution of protein biocatalysts: navigating sequence space intelligently. Chem Soc Rev 44 (2015), 1172–1239.
-
(2015)
Chem Soc Rev
, vol.44
, pp. 1172-1239
-
-
Currin, A.1
Swainston, N.2
Day, P.J.3
Kell, D.B.4
-
49
-
-
84953455884
-
Structural adaptability facilitates histidine heme ligation in a cytochrome P450
-
McIntosh, J.A., Heel, T., Buller, A.R., Chio, L., Arnold, F.H., Structural adaptability facilitates histidine heme ligation in a cytochrome P450. J Am Chem Soc 137 (2015), 13861–13865.
-
(2015)
J Am Chem Soc
, vol.137
, pp. 13861-13865
-
-
McIntosh, J.A.1
Heel, T.2
Buller, A.R.3
Chio, L.4
Arnold, F.H.5
-
50
-
-
84904464976
-
Iron porphyrin carbenes as catalytic intermediates: structures Mossbauer and NMR spectroscopic properties, and bonding
-
Khade, R.L., Fan, W., Ling, Y., Yang, L., Oldfield, E., Zhang, Y., Iron porphyrin carbenes as catalytic intermediates: structures Mossbauer and NMR spectroscopic properties, and bonding. Angew Chem Int Ed Engl 53 (2014), 7574–7578.
-
(2014)
Angew Chem Int Ed Engl
, vol.53
, pp. 7574-7578
-
-
Khade, R.L.1
Fan, W.2
Ling, Y.3
Yang, L.4
Oldfield, E.5
Zhang, Y.6
-
51
-
-
84935018556
-
Catalytic and biocatalytic iron porphyrin carbene formation: effects of binding mode, carbene substituent. Porphyrin substituent, and protein axial ligand
-
Khade, R.L., Zhang, Y., Catalytic and biocatalytic iron porphyrin carbene formation: effects of binding mode, carbene substituent. Porphyrin substituent, and protein axial ligand. J Am Chem Soc 137 (2015), 7560–7563.
-
(2015)
J Am Chem Soc
, vol.137
, pp. 7560-7563
-
-
Khade, R.L.1
Zhang, Y.2
-
52
-
-
84982737844
-
Computation sheds insight into iron porphyrin carbenes’ electronic structure, formation, and N–H insertion reactivity
-
Sharon, D.A., Mallick, D., Wang, B., Shaik, S., Computation sheds insight into iron porphyrin carbenes’ electronic structure, formation, and N–H insertion reactivity. J Am Chem Soc 138 (2016), 9597–9610.
-
(2016)
J Am Chem Soc
, vol.138
, pp. 9597-9610
-
-
Sharon, D.A.1
Mallick, D.2
Wang, B.3
Shaik, S.4
-
53
-
-
84928626673
-
Interfacing microbial styrene production with a biocompatible cyclopropanation reaction
-
Proof-of-concept study showing that bacterial production of styrene from glucose can interface with styrene cyclopropanation using a synthetic catalyst.
-
Wallace, S., Balskus, E.P., Interfacing microbial styrene production with a biocompatible cyclopropanation reaction. Angew Chem Int Ed Engl 54 (2015), 7106–7109 Proof-of-concept study showing that bacterial production of styrene from glucose can interface with styrene cyclopropanation using a synthetic catalyst.
-
(2015)
Angew Chem Int Ed Engl
, vol.54
, pp. 7106-7109
-
-
Wallace, S.1
Balskus, E.P.2
|