Beyond Iron: Iridium-Containing P450 Enzymes for Selective Cyclopropanations of Structurally Diverse Alkenes

Key, Hanna M.; Dydio, Paweł; Liu, Zhennan; Rha, Jennifer Y. -E.; Nazarenko, Andrew; Seyedkazemi, Vida; Clark, Douglas S.; Hartwig, John F.

doi:10.1021/acscentsci.6b00391

Title: Beyond Iron: Iridium-Containing P450 Enzymes for Selective Cyclopropanations of Structurally Diverse Alkenes

Journal Article · Sat Apr 01 04:00:00 UTC 2017 · ACS Central Science

DOI: https://doi.org/10.1021/acscentsci.6b00391 · OSTI ID:1349533

Key, Hanna M. ^[1];

^[1]; Liu, Zhennan ^[2]; Rha, Jennifer Y. -E. ^[2]; Nazarenko, Andrew ^[2]; Seyedkazemi, Vida ^[2]; Clark, Douglas S. ^[3];

^[1]

Department of Chemistry, University of California, Berkeley, California 94720, United States, Chemical Sciences Division, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, California 94720, United States
Department of Chemistry, University of California, Berkeley, California 94720, United States
Department of Chemical and Biomolecular Engineering, University of California, Berkeley, California 94720, United States, Molecular Biophysics and Integrated Bioimaging Division, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, California 94720, United States

Not Available

View Journal Article

Cite

Export

Save

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1349533

Journal Information:: ACS Central Science, Journal Name: ACS Central Science Journal Issue: 4 Vol. 3; ISSN 2374-7943

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (31)

A Chiral Cagelike Copper(I) Catalyst for the Highly Enantioselective Synthesis of 1,1-Cyclopropane Diesters Deng, Chao; Wang, Li-Jia; Zhu, Jun Angewandte Chemie International Edition, Vol. 51, Issue 46 https://doi.org/10.1002/anie.201206376	journal	October 2012
Improved Cyclopropanation Activity of Histidine-Ligated Cytochrome P450 Enables the Enantioselective Formal Synthesis of Levomilnacipran Wang, Z. Jane; Renata, Hans; Peck, Nicole E. Angewandte Chemie International Edition, Vol. 53, Issue 26 https://doi.org/10.1002/anie.201402809	journal	May 2014
Highly Diastereoselective and Enantioselective Olefin Cyclopropanation Using Engineered Myoglobin-Based Catalysts Bordeaux, Melanie; Tyagi, Vikas; Fasan, Rudi Angewandte Chemie International Edition, Vol. 54, Issue 6 https://doi.org/10.1002/anie.201409928	journal	December 2014
Genetic Optimization of Metalloenzymes: Enhancing Enzymes for Non-Natural Reactions Hyster, Todd K.; Ward, Thomas R. Angewandte Chemie International Edition, Vol. 55, Issue 26 https://doi.org/10.1002/anie.201508816	journal	March 2016
Gram-Scale Synthesis of Chiral Cyclopropane-Containing Drugs and Drug Precursors with Engineered Myoglobin Catalysts Featuring Complementary Stereoselectivity Bajaj, Priyanka; Sreenilayam, Gopeekrishnan; Tyagi, Vikas Angewandte Chemie International Edition, Vol. 55, Issue 52 https://doi.org/10.1002/anie.201608680	journal	November 2016
Mutating a Highly Conserved Residue in Diverse Cytochrome P450s Facilitates Diastereoselective Olefin Cyclopropanation Gober, Joshua G.; Rydeen, Amy E.; Gibson-O'Grady, Evan J. ChemBioChem, Vol. 17, Issue 5 https://doi.org/10.1002/cbic.201500624	journal	February 2016
P450 _BM3 -Axial Mutations: A Gateway to Non-Natural Reactivity Hyster, Todd K.; Arnold, Frances H. Israel Journal of Chemistry, Vol. 55, Issue 1 https://doi.org/10.1002/ijch.201400080	journal	August 2014
Enantioselective intramolecular cyclopropanation of N-allylic- and N-homoallylic diazoacetamides catalyzed by chiral dirhodium(II) catalysts Doyle, Michael P.; Eismont, Michail Y.; Protopopova, Marina N. Tetrahedron, Vol. 50, Issue 6 https://doi.org/10.1016/S0040-4020(01)80842-5	journal	January 1994
Structural control of cytochrome P450-catalyzed ω-hydroxylation Johnston, Jonathan B.; Ouellet, Hugues; Podust, Larissa M. Archives of Biochemistry and Biophysics, Vol. 507, Issue 1 https://doi.org/10.1016/j.abb.2010.08.011	journal	March 2011
An efficient synthesis of aryloxyphenyl cyclopropyl methanones: a new class of anti-mycobacterial agents Dwivedi, Namrata; Tewari, Neetu; Tiwari, V. K. Bioorganic & Medicinal Chemistry Letters, Vol. 15, Issue 20 https://doi.org/10.1016/j.bmcl.2005.07.007	journal	October 2005
Guide to enantioselective dirhodium(II)-catalyzed cyclopropanation with aryldiazoacetates Chepiga, Kathryn M.; Qin, Changming; Alford, Joshua S. Tetrahedron, Vol. 69, Issue 27-28 https://doi.org/10.1016/j.tet.2013.04.075	journal	July 2013
Enantioselective Cyclopropanation of a Wide Variety of Olefins Catalyzed by Ru(II)–Pheox Complexes Chanthamath, Soda; Iwasa, Seiji Accounts of Chemical Research, Vol. 49, Issue 10 https://doi.org/10.1021/acs.accounts.6b00070	journal	September 2016
Artificial Metalloenzymes and Metallopeptide Catalysts for Organic Synthesis Lewis, Jared C. ACS Catalysis, Vol. 3, Issue 12 https://doi.org/10.1021/cs400806a	journal	November 2013
Biocatalysis in Organic Chemistry and Biotechnology: Past, Present, and Future Reetz, Manfred T. Journal of the American Chemical Society, Vol. 135, Issue 34 https://doi.org/10.1021/ja405051f	journal	August 2013
Chemoselective, Enzymatic C–H Bond Amination Catalyzed by a Cytochrome P450 Containing an Ir(Me)-PIX Cofactor Dydio, Paweł; Key, Hanna M.; Hayashi, Hiroki Journal of the American Chemical Society, Vol. 139, Issue 5 https://doi.org/10.1021/jacs.6b11410	journal	January 2017
Chemistry and Behavioral Studies Identify Chiral Cyclopropanes as Selective α4β2-Nicotinic Acetylcholine Receptor Partial Agonists Exhibiting an Antidepressant Profile Zhang, Hankun; Tückmantel, Werner; Eaton, J. Brek Journal of Medicinal Chemistry, Vol. 55, Issue 2 https://doi.org/10.1021/jm201157c	journal	January 2012
Regioselectivity and solvent effects in cyclopropanation of alkadienes Friedrich, Edwin C.; Niyati-Shirkhodaee, Fatemeh The Journal of Organic Chemistry, Vol. 56, Issue 6 https://doi.org/10.1021/jo00006a044	journal	March 1991
Enantioselective Reactions of Donor/Acceptor Carbenoids Derived from α-Aryl-α-Diazoketones Denton, Justin R.; Davies, Huw M. L. Organic Letters, Vol. 11, Issue 4 https://doi.org/10.1021/ol802614j	journal	January 2009
Shape-selective and asymmetric cyclopropanation of alkenes catalyzed by rhodium porphyrins Maxwell, Jana L.; O'Malley, Sean; Brown, Kathlynn C. Organometallics, Vol. 11, Issue 2 https://doi.org/10.1021/om00038a023	journal	February 1992
Olefin Cyclopropanation Catalyzed by Iridium(III) Porphyrin Complexes Anding, Bernie J.; Ellern, Arkady; Woo, L. Keith Organometallics, Vol. 31, Issue 9 https://doi.org/10.1021/om300135f	journal	April 2012
Engineering the third wave of biocatalysis Bornscheuer, U. T.; Huisman, G. W.; Kazlauskas, R. J. Nature, Vol. 485, Issue 7397 https://doi.org/10.1038/nature11117	journal	May 2012
Abiological catalysis by artificial haem proteins containing noble metals in place of iron Key, Hanna M.; Dydio, Paweł; Clark, Douglas S. Nature, Vol. 534, Issue 7608 https://doi.org/10.1038/nature17968	journal	June 2016
A serine-substituted P450 catalyzes highly efficient carbene transfer to olefins in vivo Coelho, Pedro S.; Wang, Z. Jane; Ener, Maraia E. Nature Chemical Biology, Vol. 9, Issue 8 https://doi.org/10.1038/nchembio.1278	journal	June 2013
Engineering a dirhodium artificial metalloenzyme for selective olefin cyclopropanation Srivastava, Poonam; Yang, Hao; Ellis-Guardiola, Ken Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms8789	journal	July 2015
P450 _BM3 (CYP102A1): connecting the dots Whitehouse, Christopher J. C.; Bell, Stephen G.; Wong, Luet-Lok Chem. Soc. Rev., Vol. 41, Issue 3 https://doi.org/10.1039/C1CS15192D	journal	January 2012
Directed evolution of hybrid enzymes: Evolving enantioselectivity of an achiral Rh-complex anchored to a protein Reetz, Manfred T.; Peyralans, J?r?me J. -P.; Maichele, Andrea Chemical Communications, Issue 41 https://doi.org/10.1039/b610461d	journal	January 2006
Application of donor/acceptor-carbenoids to the synthesis of natural products Davies, Huw M. L.; Denton, Justin R. Chemical Society Reviews, Vol. 38, Issue 11 https://doi.org/10.1039/b901170f	journal	January 2009
Highly enantioselective intermolecular carbene insertion to C–H and Si–H bonds catalyzed by a chiral iridium(iii) complex of a D4-symmetric Halterman porphyrin ligand Wang, Jing-Cui; Xu, Zhen-Jiang; Guo, Zhen Chemical Communications, Vol. 48, Issue 36 https://doi.org/10.1039/c2cc30441d	journal	January 2012
Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes Wang, Hengbin; Guptill, David M.; Varela-Alvarez, Adrian Chemical Science, Vol. 4, Issue 7 https://doi.org/10.1039/c3sc50425e	journal	January 2013
Olefin Cyclopropanation via Carbene Transfer Catalyzed by Engineered Cytochrome P450 Enzymes Coelho, P. S.; Brustad, E. M.; Kannan, A. Science, Vol. 339, Issue 6117 https://doi.org/10.1126/science.1231434	journal	December 2012
An artificial metalloenzyme with the kinetics of native enzymes Dydio, P.; Key, H. M.; Nazarenko, A. Science, Vol. 354, Issue 6308 https://doi.org/10.1126/science.aah4427	journal	October 2016

Similar Records

P450-Mediated Non-natural Cyclopropanation of Dehydroalanine-Containing Thiopeptides

Journal Article · Tue May 23 04:00:00 UTC 2017 · ACS Chemical Biology · OSTI ID:1463727

Gober, Joshua G.; Ghodge, Swapnil V.; Bogart, Jonathan W.; +4 more

Cytochrome P450 BM3 enzyme variants for preparation of cyclopropanes

Patent · Tue May 18 04:00:00 UTC 2021 · OSTI ID:1823962

Coelho, Pedro S.; Brustad, Eric M.; Arnold, Frances H.; +2 more

Cytochrome P450 enzymes from the metabolically diverse bacterium Rhodopseudomonas palustris

Journal Article · Fri Mar 31 04:00:00 UTC 2006 · Biochemical and Biophysical Research Communications · OSTI ID:20798871

Bell, Stephen G; Hoskins, Nicola; Feng, Xu; +3 more

Title: Beyond Iron: Iridium-Containing P450 Enzymes for Selective Cyclopropanations of Structurally Diverse Alkenes

Citation Formats

References (31)

Similar Records

Related Subjects