Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using 'Ene'-Reductases with Photoredox Catalysts

Journal Article · · Angewandte Chemie (International Edition)

Research Organization:
Brookhaven National Lab. (BNL), Upton, NY (United States)
Sponsoring Organization:
~OTHER
DOE Contract Number:
SC0012704
OSTI ID:
1690061
Report Number(s):
BNL-220389-2020-JACI
Journal Information:
Angewandte Chemie (International Edition), Vol. 59, Issue 26
Publisher:
Wiley
Country of Publication:
United States
Language:
English

References (58)

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals: Miniperspective journal October 2014
Development of drugs based on imidazole and benzimidazole bioactive heterocycles: recent advances and future directions journal December 2015
Structure-activity relationship (SAR) study and design strategies of nitrogen-containing heterocyclic moieties for their anticancer activities journal January 2017
An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals journal January 2011
An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles journal January 2013
Modern advances in heterocyclic chemistry in drug discovery journal January 2016
Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands journal November 2008
Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions journal September 2016
C═N-Containing Azaarenes as Activating Groups in Enantioselective Catalysis journal December 2013
Brønsted acid-catalysed conjugate addition of photochemically generated α-amino radicals to alkenylpyridines journal January 2016
Green strategy from waste to value-added-chemical production: efficient biosynthesis of 6-hydroxy-3-succinoyl-pyridine by an engineered biocatalyst journal June 2014
Carbonyl group-dependent high-throughput screening and enzymatic characterization of diaromatic ketone reductase journal January 2016
Asymmetric whole-cell bioreduction of sterically bulky 2-benzoylpyridine derivatives in aqueous hydrophilic ionic liquid media journal May 2017
Enantioenriched Compounds via Enzyme-Catalyzed Redox Reactions journal July 2011
Biocatalysis for pharmaceutical intermediates: the future is now journal February 2007
Asymmetric bioreduction of activated alkenes to industrially relevant optically active compounds journal December 2012
Biocatalytic reduction of activated C C-bonds and beyond: emerging trends journal April 2018
Discovery, Characterization, Engineering, and Applications of Ene-Reductases for Industrial Biocatalysis journal March 2018
Accessing non-natural reactivity by irradiating nicotinamide-dependent enzymes with light journal December 2016
Photoexcitation of flavoenzymes enables a stereoselective radical cyclization journal June 2019
Asymmetric redox-neutral radical cyclization catalysed by flavin-dependent ‘ene’-reductases journal December 2019
Catalytic promiscuity enabled by photoredox catalysis in nicotinamide-dependent oxidoreductases journal June 2018
Photoenzymatic Catalysis Enables Radical‐Mediated Ketone Reduction in Ene‐Reductases journal June 2019
Photoenzymatic Catalysis Enables Radical‐Mediated Ketone Reduction in Ene‐Reductases journal May 2019
Cofactor-Free, Direct Photoactivation of Enoate Reductases for the Asymmetric Reduction of C=C Bonds journal June 2017
Cofactor-Free, Direct Photoactivation of Enoate Reductases for the Asymmetric Reduction of C=C Bonds journal June 2017
Cooperative asymmetric reactions combining photocatalysis and enzymatic catalysis journal August 2018
Combined Photoredox/Enzymatic C−H Benzylic Hydroxylations journal November 2019
Combined Photoredox/Enzymatic C−H Benzylic Hydroxylations journal September 2019
Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network journal January 2018
Enantiocomplementary decarboxylative hydroxylation combining photocatalysis and whole-cell biocatalysis in a one-pot cascade process journal January 2019
Combining Photo-Organo Redox- and Enzyme Catalysis Facilitates Asymmetric C-H Bond Functionalization: Combining Photo-Organo Redox- and Enzyme Catalysis Facilitates Asymmetric C-H Bond Functionalization journal December 2018
Light-driven biocatalytic reduction of α,β-unsaturated compounds by ene reductases employing transition metal complexes as photosensitizers journal January 2016
Photo-Biocatalysis: Biotransformations in the Presence of Light journal April 2019
Biocatalysis Fueled by Light: On the Versatile Combination of Photocatalysis and Enzymes journal June 2019
Tris(2,2'-bipyridine)ruthenium(2+)-mediated photoreduction of olefins with 1-benzyl-1,4-dihydronicotinamide: a mechanistic probe for electron-transfer reactions of NAD(P)H-model compounds journal October 1981
DiPAMP’s Big Brother “ i- Pr-SMS-Phos” Exhibits Exceptional Features Enhancing Rhodium(I)-Catalyzed Hydrogenation of Olefins journal November 2009
Pyridine-Directed Asymmetric Hydrogenation of 1,1-Diarylalkenes journal September 2017
Comparative characterization of novel ene-reductases from cyanobacteria journal January 2013
Asymmetric Bioreduction of Alkenes Using Ene–Reductases YersER and KYE1 and Effects of Organic Solvents journal May 2011
Artificial metalloenzymes for enantioselective catalysis: the phenomenon of protein accelerated catalysis journal December 2004
Biotinylated Rh(III) Complexes in Engineered Streptavidin for Accelerated Asymmetric C-H Activation journal October 2012
Enantioselective Hydrogen Atom Transfer: Discovery of Catalytic Promiscuity in Flavin-Dependent ‘Ene’-Reductases journal August 2017
Site-Saturation Mutagenesis of Tryptophan 116 of Saccharomyces pastorianus Old Yellow Enzyme Uncovers Stereocomplementary Variants journal March 2009
Interaction of phenols with old yellow enzyme. Physical evidence for charge-transfer complexes. journal September 1976
The Persistent Radical Effect in Organic Synthesis journal January 2020
Der “Persistent Radical Effect” in der organischen Chemie journal January 2020
Polycyano Radicals journal August 1966
Structural aspects of the mechanical and thermal dissociation of the central bond in 2,2′-bis(2,3,4-triarylchromenyl)s journal January 1992
Sterically hindered free radicals. Part 22. Dimerization and EPR spectroscopy of indanedionyl and 9-acylfluorenyl radicals journal January 1994
Bond Dissociation Energies for Radical Dimers Derived from Highly Stabilized Carbon-Centered Radicals journal July 2004
Self-Healing of Chemical Gels Cross-Linked by Diarylbibenzofuranone-Based Trigger-Free Dynamic Covalent Bonds at Room Temperature journal November 2011
Self-Healing of Chemical Gels Cross-Linked by Diarylbibenzofuranone-Based Trigger-Free Dynamic Covalent Bonds at Room Temperature journal November 2011
N-Substituted Dicyanomethylphenyl Radicals: Dynamic Covalent Properties and Formation of Stimuli-Responsive Cyclophanes by Self-Assembly journal June 2016
N-Substituted Dicyanomethylphenyl Radicals: Dynamic Covalent Properties and Formation of Stimuli-Responsive Cyclophanes by Self-Assembly journal June 2016
NIR mechanochromic behaviours of a tetracyanoethylene-bridged hexa-peri-hexabenzocoronene dimer and trimer through dissociation of C–C bonds journal January 2017
Effect of Substituents on the Bond Strength of Air-Stable Dicyanomethyl Radical Thermochromes journal June 2017
Cross‐Coupling Reaction of Dimer‐Derived Persistent Tertiary‐Carbon‐Centered Radicals with Azo Compounds journal March 2019