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

Journal Article · · ACS Central Science
 [1];  [1];  [2];  [2];  [2];  [2];  [3];  [1]
  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
  2. Department of Chemistry, University of California, Berkeley, California 94720, United States
  3. 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

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

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Highly Diastereoselective and Enantioselective Olefin Cyclopropanation Using Engineered Myoglobin-Based Catalysts journal December 2014
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Gram-Scale Synthesis of Chiral Cyclopropane-Containing Drugs and Drug Precursors with Engineered Myoglobin Catalysts Featuring Complementary Stereoselectivity journal November 2016
Mutating a Highly Conserved Residue in Diverse Cytochrome P450s Facilitates Diastereoselective Olefin Cyclopropanation journal February 2016
P450 BM3 -Axial Mutations: A Gateway to Non-Natural Reactivity journal August 2014
Enantioselective intramolecular cyclopropanation of N-allylic- and N-homoallylic diazoacetamides catalyzed by chiral dirhodium(II) catalysts journal January 1994
Structural control of cytochrome P450-catalyzed ω-hydroxylation journal March 2011
An efficient synthesis of aryloxyphenyl cyclopropyl methanones: a new class of anti-mycobacterial agents journal October 2005
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Enantioselective Cyclopropanation of a Wide Variety of Olefins Catalyzed by Ru(II)–Pheox Complexes journal September 2016
Artificial Metalloenzymes and Metallopeptide Catalysts for Organic Synthesis journal November 2013
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Chemoselective, Enzymatic C–H Bond Amination Catalyzed by a Cytochrome P450 Containing an Ir(Me)-PIX Cofactor journal January 2017
Chemistry and Behavioral Studies Identify Chiral Cyclopropanes as Selective α4β2-Nicotinic Acetylcholine Receptor Partial Agonists Exhibiting an Antidepressant Profile journal January 2012
Regioselectivity and solvent effects in cyclopropanation of alkadienes journal March 1991
Enantioselective Reactions of Donor/Acceptor Carbenoids Derived from α-Aryl-α-Diazoketones journal January 2009
Shape-selective and asymmetric cyclopropanation of alkenes catalyzed by rhodium porphyrins journal February 1992
Olefin Cyclopropanation Catalyzed by Iridium(III) Porphyrin Complexes journal April 2012
Engineering the third wave of biocatalysis journal May 2012
Abiological catalysis by artificial haem proteins containing noble metals in place of iron journal June 2016
A serine-substituted P450 catalyzes highly efficient carbene transfer to olefins in vivo journal June 2013
Engineering a dirhodium artificial metalloenzyme for selective olefin cyclopropanation journal July 2015
P450 BM3 (CYP102A1): connecting the dots journal January 2012
Directed evolution of hybrid enzymes: Evolving enantioselectivity of an achiral Rh-complex anchored to a protein journal January 2006
Application of donor/acceptor-carbenoids to the synthesis of natural products 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 journal January 2012
Rhodium-catalyzed enantioselective cyclopropanation of electron-deficient alkenes journal January 2013
Olefin Cyclopropanation via Carbene Transfer Catalyzed by Engineered Cytochrome P450 Enzymes journal December 2012
An artificial metalloenzyme with the kinetics of native enzymes journal October 2016

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