Enantioselective Enzymatic Reduction of Acrylic Acids.

An ene-reductase (ERED 36) with broad substrate specificity was identified, and optimization studies led to the development of an enzymatic protocol for the reduction of α,β-unsaturated acids under mild, aqueous conditions. The substrate scope includes aromatic- and aliphatic-substituted acrylic acids, as well as cyclic α,β-substituted acrylic acids, yielding chiral α-substituted acids with exquisite levels of enantioselectivity (>99% ee).

[1]  M. Hall,et al.  Biocatalytic reduction of activated CC-bonds and beyond: emerging trends. , 2018, Current opinion in chemical biology.

[2]  N. Selmi,et al.  Discovery of AZD2716: A Novel Secreted Phospholipase A2 (sPLA2) Inhibitor for the Treatment of Coronary Artery Disease , 2016, ACS medicinal chemistry letters.

[3]  Rachit Jain,et al.  Aerobic biosynthesis of hydrocinnamic acids in Escherichia coli with a strictly oxygen-sensitive enoate reductase. , 2016, Metabolic engineering.

[4]  Delong Liu,et al.  Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline-Ruthenium Complex. , 2016, Organic letters.

[5]  Staffan Karlsson,et al.  An Enantioselective Hydrogenation of an Alkenoic Acid as a Key Step in the Synthesis of AZD2716 , 2016 .

[6]  S. Sieber,et al.  Phenyl Esters Are Potent Inhibitors of Caseinolytic Protease P and Reveal a Stereogenic Switch for Deoligomerization. , 2015, Journal of the American Chemical Society.

[7]  H. Gröger,et al.  The Organic–Synthetic Potential of Recombinant Ene Reductases: Substrate‐Scope Evaluation and Process Optimization , 2015 .

[8]  Nigel S Scrutton,et al.  New developments in 'ene'-reductase catalysed biological hydrogenations. , 2014, Current opinion in chemical biology.

[9]  G. Tasnádi,et al.  Asymmetric bioreduction of activated alkenes to industrially relevant optically active compounds , 2012, Journal of biotechnology.

[10]  K. Zangger,et al.  Unusual C=C Bond Isomerization of an α,β-Unsaturated γ-Butyrolactone Catalysed by Flavoproteins from the Old Yellow Enzyme Family , 2012, Chembiochem : a European journal of chemical biology.

[11]  Shou‐Fei Zhu,et al.  Enantioselective hydrogenation of α-substituted acrylic acids catalyzed by iridium complexes with chiral spiro aminophosphine ligands. , 2012, Angewandte Chemie.

[12]  P. Macheroux,et al.  Stereocomplementary bioreduction of alpha,beta-unsaturated dicarboxylic acids and dimethyl esters using enoate reductases: enzyme- and substrate-based stereocontrol. , 2007, Organic letters.

[13]  P. Macheroux,et al.  Asymmetric bioreduction of activated alkenes using cloned 12-oxophytodienoate reductase isoenzymes OPR-1 and OPR-3 from Lycopersicon esculentum (tomato): a striking change of stereoselectivity. , 2007, Angewandte Chemie.

[14]  W. Metcalf,et al.  Phosphite dehydrogenase: an unusual phosphoryl transfer reaction. , 2001, Journal of the American Chemical Society.

[15]  P. Karplus,et al.  On the Active Site of Old Yellow Enzyme , 1998, The Journal of Biological Chemistry.

[16]  V. Massey,et al.  The Oxidative Half-reaction of Old Yellow Enzyme , 1998, The Journal of Biological Chemistry.

[17]  Andrube Harrington,et al.  Twenty Years of Naproxen Technology , 1997 .

[18]  Chi‐Huey Wong,et al.  Enzymatic vs. fermentative synthesis: thermostable glucose dehydrogenase catalyzed regeneration of NAD(P)H for use in enzymatic synthesis , 1985 .

[19]  D. Evans,et al.  Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates , 1981 .

[20]  W. Tischer,et al.  Purification and Some Properties of a Hitherto‐Unknown Enzyme Reducing the Carbon‐Carbon Double Bond of α,β‐Unsaturated Carboxylate Anions , 1979 .

[21]  S. Noguchi,et al.  1-Indancarboxylic acids. IV. A convenient synthesis of antiinflammatory 4-aroyl-1-indancarboxylic acids and their absolute configurations. , 1978, Chemical & pharmaceutical bulletin.

[22]  T. Hudyma,et al.  Antiinflammatory activity of some indan-1-carboxylic acids and related compounds. , 1972, Journal of medicinal chemistry.