Chemoenzymatic Platform for Synthesis of Chiral Organofluorines Based on Type II Aldolases
- Authors:
-
[1];
[1];
[1];
[2]
- Department of Chemistry University of California, Berkeley Berkeley CA 94720 USA, Chemical Sciences Division Laurence Berkeley National Laboratory Berkeley CA 94720 USA
- Department of Chemistry University of California, Berkeley Berkeley CA 94720 USA, Chemical Sciences Division Laurence Berkeley National Laboratory Berkeley CA 94720 USA, Department of Molecular &, Cell Biology University of California, Berkeley Berkeley CA 94720 USA
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1543163
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Angewandte Chemie (International Edition)
- Additional Journal Information:
- Journal Name: Angewandte Chemie (International Edition) Journal Volume: 58 Journal Issue: 34; Journal ID: ISSN 1433-7851
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Fang, Jason, Hait, Diptarka, Head‐Gordon, Martin, and Chang, Michelle C. Y. Chemoenzymatic Platform for Synthesis of Chiral Organofluorines Based on Type II Aldolases. Germany: N. p., 2019.
Web. doi:10.1002/anie.201906805.
Fang, Jason, Hait, Diptarka, Head‐Gordon, Martin, & Chang, Michelle C. Y. Chemoenzymatic Platform for Synthesis of Chiral Organofluorines Based on Type II Aldolases. Germany. https://doi.org/10.1002/anie.201906805
Fang, Jason, Hait, Diptarka, Head‐Gordon, Martin, and Chang, Michelle C. Y. Fri .
"Chemoenzymatic Platform for Synthesis of Chiral Organofluorines Based on Type II Aldolases". Germany. https://doi.org/10.1002/anie.201906805.
@article{osti_1543163,
title = {Chemoenzymatic Platform for Synthesis of Chiral Organofluorines Based on Type II Aldolases},
author = {Fang, Jason and Hait, Diptarka and Head‐Gordon, Martin and Chang, Michelle C. Y.},
abstractNote = {},
doi = {10.1002/anie.201906805},
journal = {Angewandte Chemie (International Edition)},
number = 34,
volume = 58,
place = {Germany},
year = {2019},
month = {7}
}
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https://doi.org/10.1002/anie.201906805
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Works referenced in this record:
The synthetic utility of KDPGal aldolase
journal, September 1998
- Cotterill, Ian C.; Henderson, Darla P.; Shelton, Michael C.
- Journal of Molecular Catalysis B: Enzymatic, Vol. 5, Issue 1-4
C−C Bond-Forming Lyases in Organic Synthesis
journal, July 2011
- Brovetto, Margarita; Gamenara, Daniela; Saenz Méndez, Patricia
- Chemical Reviews, Vol. 111, Issue 7
The direct catalytic asymmetric aldol reaction
journal, January 2010
- Trost, Barry M.; Brindle, Cheyenne S.
- Chemical Society Reviews, Vol. 39, Issue 5
Biocatalytic Methods for CC Bond Formation
journal, February 2013
- Fesko, Kateryna; Gruber-Khadjawi, Mandana
- ChemCatChem, Vol. 5, Issue 6
Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli
journal, February 2018
- Hernández, Karel; Joglar, Jesús; Bujons, Jordi
- Angewandte Chemie International Edition, Vol. 57, Issue 14
An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters
journal, April 2016
- Howard, James K.; Müller, Marion; Berry, Alan
- Angewandte Chemie, Vol. 128, Issue 23
Fluorine in medicinal chemistry
journal, January 2008
- Purser, Sophie; Moore, Peter R.; Swallow, Steve
- Chem. Soc. Rev., Vol. 37, Issue 2
Enzymes for chemical synthesis
journal, January 2001
- Koeller, Kathryn M.; Wong, Chi-Huey
- Nature, Vol. 409, Issue 6817
Crystal Structure of Reaction Intermediates in Pyruvate Class II Aldolase: SUBSTRATE CLEAVAGE, ENOLATE STABILIZATION, AND SUBSTRATE SPECIFICITY
journal, August 2012
- Coincon, Mathieu; Wang, Weijun; Sygusch, Jurgen
- Journal of Biological Chemistry, Vol. 287, Issue 43
The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases
journal, January 2014
- Fateev, Ilja V.; Antonov, Konstantin V.; Konstantinova, Irina D.
- Beilstein Journal of Organic Chemistry, Vol. 10
Enantioselektive Chemo- und Biokatalyse: Partner in der Retrosynthese
journal, June 2017
- Hönig, Moritz; Sondermann, Philipp; Turner, Nicholas J.
- Angewandte Chemie, Vol. 129, Issue 31
Engineered Fluorine Metabolism and Fluoropolymer Production in Living Cells
journal, September 2017
- Thuronyi, Benjamin W.; Privalsky, Thomas M.; Chang, Michelle C. Y.
- Angewandte Chemie International Edition, Vol. 56, Issue 44
Purification and Biochemical Characterization of a Pyruvate-Specific Class II Aldolase, HpaI †
journal, July 2005
- Wang, Weijun; Seah, Stephen Y. K.
- Biochemistry, Vol. 44, Issue 27
Introduction of Fluorine and Fluorine-Containing Functional Groups
journal, July 2013
- Liang, Theresa; Neumann, Constanze N.; Ritter, Tobias
- Angewandte Chemie International Edition, Vol. 52, Issue 32
Combining Aldolases and Transaminases for the Synthesis of 2-Amino-4-hydroxybutanoic Acid
journal, February 2017
- Hernandez, Karel; Bujons, Jordi; Joglar, Jesús
- ACS Catalysis, Vol. 7, Issue 3
Crystal structure of a bifunctional aldolase-dehydrogenase: Sequestering a reactive and volatile intermediate
journal, May 2003
- Manjasetty, B. A.; Powlowski, J.; Vrielink, A.
- Proceedings of the National Academy of Sciences, Vol. 100, Issue 12
Asymmetric synthesis of (R)-3-fluoroalanine from 3-fluoropyruvate using omega-transaminase
journal, April 2011
- Bea, Han-Seop; Lee, Sang-Hyeup; Yun, Hyungdon
- Biotechnology and Bioprocess Engineering, Vol. 16, Issue 2
Crystal Structure and Functional Assignment of YfaU, a Metal Ion Dependent Class II Aldolase from Escherichia coli K12 † ‡
journal, September 2008
- Rea, Dean; Hovington, Rebecca; Rakus, John F.
- Biochemistry, Vol. 47, Issue 38
Expanding the reaction space of aldolases using hydroxypyruvate as a nucleophilic substrate
journal, January 2017
- de Berardinis, Véronique; Guérard-Hélaine, Christine; Darii, Ekaterina
- Green Chemistry, Vol. 19, Issue 2
An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters
journal, April 2016
- Howard, James K.; Müller, Marion; Berry, Alan
- Angewandte Chemie International Edition, Vol. 55, Issue 23
Evolution of Enzymatic Activities in the Enolase Superfamily: Characterization of the ( D )-Glucarate/Galactarate Catabolic Pathway in Escherichia coli †
journal, October 1998
- Hubbard, Brian K.; Koch, Marjan; Palmer, David R. J.
- Biochemistry, Vol. 37, Issue 41
Comparison of Two Metal-Dependent Pyruvate Aldolases Related by Convergent Evolution: Substrate Specificity, Kinetic Mechanism, and Substrate Channeling
journal, May 2010
- Wang, Weijun; Baker, Perrin; Seah, Stephen Y. K.
- Biochemistry, Vol. 49, Issue 17
Catalytic enantioselective aldol reactions
journal, January 2018
- Yamashita, Yasuhiro; Yasukawa, Tomohiro; Yoo, Woo-Jin
- Chemical Society Reviews, Vol. 47, Issue 12
Recent Advances in Aldolase-Catalyzed Asymmetric Synthesis
journal, June 2007
- Dean, Stephen M.; Greenberg, William A.; Wong, Chi-Huey
- Advanced Synthesis & Catalysis, Vol. 349, Issue 8-9
Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli
journal, February 2018
- Hernández, Karel; Joglar, Jesús; Bujons, Jordi
- Angewandte Chemie, Vol. 130, Issue 14
Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions
journal, August 2014
- Yang, Xiaoyu; Wu, Tao; Phipps, Robert J.
- Chemical Reviews, Vol. 115, Issue 2
Evaluation of fluoropyruvate as nucleophile in reactions catalysed by N-acetyl neuraminic acid lyase variants: scope, limitations and stereoselectivity
journal, January 2016
- Stockwell, Jennifer; Daniels, Adam D.; Windle, Claire L.
- Organic & Biomolecular Chemistry, Vol. 14, Issue 1
Crystal structures of the metal-dependent 2-dehydro-3-deoxy-galactarate aldolase suggest a novel reaction mechanism
journal, August 2000
- Izard, Tina; Blackwell, Nicholas C.
- The EMBO Journal, Vol. 19, Issue 15
Mechanism-based inhibition of an aldolase at high concentrations of its natural substrate acetaldehyde: structural insights and protective strategies
journal, January 2016
- Dick, Markus; Hartmann, Rudolf; Weiergräber, Oliver H.
- Chemical Science, Vol. 7, Issue 7
Engineered Fluorine Metabolism and Fluoropolymer Production in Living Cells
journal, September 2017
- Thuronyi, Benjamin W.; Privalsky, Thomas M.; Chang, Michelle C. Y.
- Angewandte Chemie, Vol. 129, Issue 44
Aldolase-catalysed stereoselective synthesis of fluorinated small molecules
journal, April 2017
- Windle, Claire L.; Berry, Alan; Nelson, Adam
- Current Opinion in Chemical Biology, Vol. 37
Organic fluorine compounds: a great opportunity for enhanced materials properties
journal, January 2011
- Berger, Ricarda; Resnati, Giuseppe; Metrangolo, Pierangelo
- Chemical Society Reviews, Vol. 40, Issue 7
2-Keto-3-Deoxy- l -Rhamnonate Aldolase (YfaU) as Catalyst in Aldol Additions of Pyruvate to Amino Aldehyde Derivatives
journal, May 2017
- Hernández, Karel; Gómez, Ariadna; Joglar, Jesús
- Advanced Synthesis & Catalysis, Vol. 359, Issue 12
Structure and Mechanism of HpcH: A Metal Ion Dependent Class II Aldolase from the Homoprotocatechuate Degradation Pathway of Escherichia coli
journal, November 2007
- Rea, Dean; Fülöp, Vilmos; Bugg, Timothy D. H.
- Journal of Molecular Biology, Vol. 373, Issue 4
Purification and Gene Cloning of -Methylserine Aldolase from Ralstonia sp. Strain AJ110405 and Application of the Enzyme in the Synthesis of -Methyl-L-Serine
journal, October 2008
- Nozaki, H.; Kuroda, S.; Watanabe, K.
- Applied and Environmental Microbiology, Vol. 74, Issue 24
Fluorine in Pharmaceuticals: Looking Beyond Intuition
journal, September 2007
- Muller, K.; Faeh, C.; Diederich, F.
- Science, Vol. 317, Issue 5846
Einführung von Fluor und fluorhaltigen funktionellen Gruppen
journal, July 2013
- Liang, Theresa; Neumann, Constanze N.; Ritter, Tobias
- Angewandte Chemie, Vol. 125, Issue 32
Expanding the Fluorine Chemistry of Living Systems Using Engineered Polyketide Synthase Pathways
journal, September 2013
- Walker, M. C.; Thuronyi, B. W.; Charkoudian, L. K.
- Science, Vol. 341, Issue 6150
Eukaryotic and Bacterial Gene Clusters Related to an Alternative Pathway of Nonphosphorylated L-Rhamnose Metabolism
journal, May 2008
- Watanabe, Seiya; Saimura, Masayuki; Makino, Keisuke
- Journal of Biological Chemistry, Vol. 283, Issue 29
Enantioselective Chemo- and Biocatalysis: Partners in Retrosynthesis
journal, June 2017
- Hönig, Moritz; Sondermann, Philipp; Turner, Nicholas J.
- Angewandte Chemie International Edition, Vol. 56, Issue 31
Enantioselective aldol reactions with masked fluoroacetates
journal, January 2016
- Saadi, Jakub; Wennemers, Helma
- Nature Chemistry, Vol. 8, Issue 3