Chemoenzymatic Platform for Synthesis of Chiral Organofluorines Based on Type II Aldolases

doi:10.1002/anie.201906805

This content will become publicly available on July 18, 2020

Title: Chemoenzymatic Platform for Synthesis of Chiral Organofluorines Based on Type II Aldolases

Authors:

^[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:: 2019-07-19

Sponsoring Org.:: USDOE

OSTI Identifier:: 1543163

Grant/Contract Number:: AC02-05CH11231

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.

Copy to clipboard


                    Fang, Jason, Hait, Diptarka, Head-Gordon, Martin, & Chang, Michelle C. Y. Chemoenzymatic Platform for Synthesis of Chiral Organofluorines Based on Type II Aldolases.  Germany.  doi:10.1002/anie.201906805.

Copy to clipboard


                    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.  doi:10.1002/anie.201906805.

Copy to clipboard


                    
@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}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

This content will become publicly available on July 18, 2020

Publisher's Version of Record

DOI: 10.1002/anie.201906805

Other availability

Search WorldCat to find libraries that may hold this journal

Save / Share:

Export Metadata

Save to My Library

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
DOI: 10.1016/S1381-1177(98)00087-3

C−C Bond-Forming Lyases in Organic Synthesis
journal, July 2011

Brovetto, Margarita; Gamenara, Daniela; Saenz Méndez, Patricia
Chemical Reviews, Vol. 111, Issue 7
DOI: 10.1021/cr100299p

The direct catalytic asymmetric aldol reaction
journal, January 2010

Trost, Barry M.; Brindle, Cheyenne S.
Chemical Society Reviews, Vol. 39, Issue 5
DOI: 10.1039/b923537j

Biocatalytic Methods for CC Bond Formation
journal, February 2013

Fesko, Kateryna; Gruber-Khadjawi, Mandana
ChemCatChem, Vol. 5, Issue 6
DOI: 10.1002/cctc.201200709

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
DOI: 10.1002/anie.201711289

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
DOI: 10.1002/ange.201602852

Fluorine in medicinal chemistry
journal, January 2008

Purser, Sophie; Moore, Peter R.; Swallow, Steve
Chem. Soc. Rev., Vol. 37, Issue 2
DOI: 10.1039/B610213C

Enzymes for chemical synthesis
journal, January 2001

Koeller, Kathryn M.; Wong, Chi-Huey
Nature, Vol. 409, Issue 6817
DOI: 10.1038/35051706

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
DOI: 10.1074/jbc.M112.400705

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
DOI: 10.3762/bjoc.10.173

Enantioselektive Chemo- und Biokatalyse: Partner in der Retrosynthese
journal, June 2017

Hönig, Moritz; Sondermann, Philipp; Turner, Nicholas J.
Angewandte Chemie, Vol. 129, Issue 31
DOI: 10.1002/ange.201612462

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
DOI: 10.1002/anie.201706696

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
DOI: 10.1021/bi050607y

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
DOI: 10.1002/anie.201206566

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
DOI: 10.1021/acscatal.6b03181

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
DOI: 10.1073/pnas.1236794100

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
DOI: 10.1007/s12257-010-0282-x

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
DOI: 10.1021/bi800943g

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
DOI: 10.1039/C6GC02652D

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
DOI: 10.1002/anie.201602852

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
DOI: 10.1021/bi981124f

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
DOI: 10.1021/bi100251u

Catalytic enantioselective aldol reactions
journal, January 2018

Yamashita, Yasuhiro; Yasukawa, Tomohiro; Yoo, Woo-Jin
Chemical Society Reviews, Vol. 47, Issue 12
DOI: 10.1039/C7CS00824D

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
DOI: 10.1002/adsc.200700115

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
DOI: 10.1002/ange.201711289

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
DOI: 10.1021/cr500277b

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
DOI: 10.1039/C5OB02037A

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
DOI: 10.1093/emboj/19.15.3849

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
DOI: 10.1039/C5SC04574F

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
DOI: 10.1002/ange.201706696

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
DOI: 10.1016/j.cbpa.2016.12.029

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
DOI: 10.1039/c0cs00221f

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
DOI: 10.1002/adsc.201700360

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
DOI: 10.1016/j.jmb.2007.06.048

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
DOI: 10.1128/AEM.00677-08

Fluorine in Pharmaceuticals: Looking Beyond Intuition
journal, September 2007

Muller, K.; Faeh, C.; Diederich, F.
Science, Vol. 317, Issue 5846
DOI: 10.1126/science.1131943

Einführung von Fluor und fluorhaltigen funktionellen Gruppen
journal, July 2013

Liang, Theresa; Neumann, Constanze N.; Ritter, Tobias
Angewandte Chemie, Vol. 125, Issue 32
DOI: 10.1002/ange.201206566

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
DOI: 10.1126/science.1242345

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
DOI: 10.1074/jbc.M801065200

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
DOI: 10.1002/anie.201612462

Enantioselective aldol reactions with masked fluoroacetates
journal, January 2016

Saadi, Jakub; Wennemers, Helma
Nature Chemistry, Vol. 8, Issue 3
DOI: 10.1038/nchem.2437

Similar records in OSTI.GOV collections:

Rational Design Synthesis and Evaluation of New Selective Inhibitors of Microbial Class II (Zinc Dependent) Fructose Bis-phosphate Aldolases

Journal Article R Daher ; M Coincon ; M Fonvielle ; ... - Journal of Medicinal Chemistry

We report the synthesis and biochemical evaluation of several selective inhibitors of class II (zinc dependent) fructose bis-phosphate aldolases (Fba). The products were designed as transition-state analogues of the catalyzed reaction, structurally related to the substrate fructose bis-phosphate (or sedoheptulose bis-phosphate) and based on an N-substituted hydroxamic acid, as a chelator of the zinc ion present in active site. The compounds synthesized were tested on class II Fbas from various pathogenic microorganisms and, by comparison, on a mammalian class I Fba. The best inhibitor shows Ki against class II Fbas from various pathogens in the nM range, with very highmore »« less
Structural and functional characterization of methicillin-resistant Staphylococcus aureus’s class IIb fructose 1,6-bisphosphate aldolase

Journal Article Capodagli, Glenn C. ; Lee, Stephen A. ; Boehm, Kyle J. ; ... - Biochemistry

Staphylococcus aureus is one of the most common nosocomial sources of soft-tissue and skin infections and has more recently become prevalent in the community setting as well. Since the use of penicillins to combat S. aureus infections in the 1940s, the bacterium has been notorious for developing resistances to antibiotics, such as methicillin-resistant Staphylococcus aureus (MRSA). With the persistence of MRSA as well as many other drug resistant bacteria and parasites, there is a growing need to focus on new pharmacological targets. Recently, class II fructose 1,6-bisphosphate aldolases (FBAs) have garnered attention to fill this role. Regrettably, scarce biochemical datamore »« less
Cited by 4
DOI: 10.1021/bi501141t
Structural and functional characterization of methicillin-resistant Staphylococcus aureus’s class IIb fructose 1,6-bisphosphate aldolase

Journal Article Capodagli, Glenn C. ; Lee, Stephen A. ; Boehm, Kyle J. ; ... - Biochemistry

Staphylococcus aureus is one of the most common nosocomial sources of soft-tissue and skin infections and has more recently become prevalent in the community setting as well. Since the use of penicillins to combat S. aureus infections in the 1940s, the bacterium has been notorious for developing resistances to antibiotics, such as methicillin-resistant Staphylococcus aureus (MRSA). With the persistence of MRSA as well as many other drug resistant bacteria and parasites, there is a growing need to focus on new pharmacological targets. Recently, class II fructose 1,6-bisphosphate aldolases (FBAs) have garnered attention to fill this role. Regrettably, scarce biochemical datamore »« less
Cited by 4
DOI: 10.1021/bi501141t

Full Text Available
3D MoS ₂ Aerogel for Ultrasensitive NO ₂ Detection and Its Tunable Sensing Behavior

Journal Article Long, Hu ; Chan, Leslie ; Harley-Trochimczyk, Anna ; ... - Advanced Materials Interfaces

A high-performance NO ₂ sensor based on the 3D MoS ₂ aerogel is introduced. Compared to single- or few-layer MoS2, 3D assemblies of 2D MoS ₂ provide more surface area per footprint with a simple and scalable synthesis. Integration of the 3D MoS ₂ aerogel on a low-power microheater platform is demonstrated, and the sensing behavior of the 3D MoS ₂ aerogel is investigated. A two-step sulfurization treatment is developed to obtain a high-quality MoS ₂ aerogel with strong sensing performance. The aerogel exhibits low detection limit (50 ppb) toward NO ₂ at room temperature, while after the two-step sulfurizationmore »« less
Cited by 6
DOI: 10.1002/admi.201700217

Full Text Available
Unconventional Chiral Fermions and Large Topological Fermi Arcs in RhSi

Journal Article Chang, Guoqing ; Xu, Su-Yang ; Wieder, Benjamin J. ; ... - Physical Review Letters

The theoretical proposal of chiral fermions in topological semimetals has led to a significant effort towards their experimental realization. In particular, the Fermi surfaces of chiral semimetals carry quantized Chern numbers, making them an attractive platform for the observation of exotic transport and optical phenomena. Although the simplest example of a chiral fermion in condensed matter is a conventional |C|=1 Weyl fermion, recent theoretical works have proposed a number of unconventional chiral fermions beyond the standard model which are protected by unique combinations of topology and crystalline symmetries. Yet, materials candidates for experimentally probing the transport and response signatures ofmore »« less
Cited by 25
DOI: 10.1103/PhysRevLett.119.206401

Full Text Available

Similar Records

This content will become publicly available on July 18, 2020

Title: Chemoenzymatic Platform for Synthesis of Chiral Organofluorines Based on Type II Aldolases

Citation Formats

The synthetic utility of KDPGal aldolase journal, September 1998

C−C Bond-Forming Lyases in Organic Synthesis journal, July 2011

The direct catalytic asymmetric aldol reaction journal, January 2010

Biocatalytic Methods for CC Bond Formation journal, February 2013

Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli journal, February 2018

An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters journal, April 2016

Fluorine in medicinal chemistry journal, January 2008

Enzymes for chemical synthesis journal, January 2001

Crystal Structure of Reaction Intermediates in Pyruvate Class II Aldolase: SUBSTRATE CLEAVAGE, ENOLATE STABILIZATION, AND SUBSTRATE SPECIFICITY journal, August 2012

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

Enantioselektive Chemo- und Biokatalyse: Partner in der Retrosynthese journal, June 2017

Engineered Fluorine Metabolism and Fluoropolymer Production in Living Cells journal, September 2017

Purification and Biochemical Characterization of a Pyruvate-Specific Class II Aldolase, HpaI † journal, July 2005

Introduction of Fluorine and Fluorine-Containing Functional Groups journal, July 2013

Combining Aldolases and Transaminases for the Synthesis of 2-Amino-4-hydroxybutanoic Acid journal, February 2017

Crystal structure of a bifunctional aldolase-dehydrogenase: Sequestering a reactive and volatile intermediate journal, May 2003

Asymmetric synthesis of (R)-3-fluoroalanine from 3-fluoropyruvate using omega-transaminase journal, April 2011

Crystal Structure and Functional Assignment of YfaU, a Metal Ion Dependent Class II Aldolase from Escherichia coli K12 † ‡ journal, September 2008

Expanding the reaction space of aldolases using hydroxypyruvate as a nucleophilic substrate journal, January 2017

An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters journal, April 2016

Evolution of Enzymatic Activities in the Enolase Superfamily: Characterization of the ( D )-Glucarate/Galactarate Catabolic Pathway in Escherichia coli † journal, October 1998

Comparison of Two Metal-Dependent Pyruvate Aldolases Related by Convergent Evolution: Substrate Specificity, Kinetic Mechanism, and Substrate Channeling journal, May 2010

Catalytic enantioselective aldol reactions journal, January 2018

Recent Advances in Aldolase-Catalyzed Asymmetric Synthesis journal, June 2007

Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli journal, February 2018

Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions journal, August 2014

Evaluation of fluoropyruvate as nucleophile in reactions catalysed by N-acetyl neuraminic acid lyase variants: scope, limitations and stereoselectivity journal, January 2016

Crystal structures of the metal-dependent 2-dehydro-3-deoxy-galactarate aldolase suggest a novel reaction mechanism journal, August 2000

Mechanism-based inhibition of an aldolase at high concentrations of its natural substrate acetaldehyde: structural insights and protective strategies journal, January 2016

Engineered Fluorine Metabolism and Fluoropolymer Production in Living Cells journal, September 2017

Aldolase-catalysed stereoselective synthesis of fluorinated small molecules journal, April 2017

Organic fluorine compounds: a great opportunity for enhanced materials properties journal, January 2011

2-Keto-3-Deoxy- l -Rhamnonate Aldolase (YfaU) as Catalyst in Aldol Additions of Pyruvate to Amino Aldehyde Derivatives journal, May 2017

Structure and Mechanism of HpcH: A Metal Ion Dependent Class II Aldolase from the Homoprotocatechuate Degradation Pathway of Escherichia coli journal, November 2007

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

Fluorine in Pharmaceuticals: Looking Beyond Intuition journal, September 2007

Einführung von Fluor und fluorhaltigen funktionellen Gruppen journal, July 2013

Expanding the Fluorine Chemistry of Living Systems Using Engineered Polyketide Synthase Pathways journal, September 2013

Eukaryotic and Bacterial Gene Clusters Related to an Alternative Pathway of Nonphosphorylated L-Rhamnose Metabolism journal, May 2008

Enantioselective Chemo- and Biocatalysis: Partners in Retrosynthesis journal, June 2017

Enantioselective aldol reactions with masked fluoroacetates journal, January 2016

The synthetic utility of KDPGal aldolase
journal, September 1998

C−C Bond-Forming Lyases in Organic Synthesis
journal, July 2011

The direct catalytic asymmetric aldol reaction
journal, January 2010

Biocatalytic Methods for CC Bond Formation
journal, February 2013

Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli
journal, February 2018

An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters
journal, April 2016

Fluorine in medicinal chemistry
journal, January 2008

Enzymes for chemical synthesis
journal, January 2001

Crystal Structure of Reaction Intermediates in Pyruvate Class II Aldolase: SUBSTRATE CLEAVAGE, ENOLATE STABILIZATION, AND SUBSTRATE SPECIFICITY
journal, August 2012

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

Enantioselektive Chemo- und Biokatalyse: Partner in der Retrosynthese
journal, June 2017

Engineered Fluorine Metabolism and Fluoropolymer Production in Living Cells
journal, September 2017

Purification and Biochemical Characterization of a Pyruvate-Specific Class II Aldolase, HpaI ^†
journal, July 2005

Introduction of Fluorine and Fluorine-Containing Functional Groups
journal, July 2013

Combining Aldolases and Transaminases for the Synthesis of 2-Amino-4-hydroxybutanoic Acid
journal, February 2017

Crystal structure of a bifunctional aldolase-dehydrogenase: Sequestering a reactive and volatile intermediate
journal, May 2003

Asymmetric synthesis of (R)-3-fluoroalanine from 3-fluoropyruvate using omega-transaminase
journal, April 2011

Crystal Structure and Functional Assignment of YfaU, a Metal Ion Dependent Class II Aldolase from Escherichia coli K12 ^† ^‡
journal, September 2008

Expanding the reaction space of aldolases using hydroxypyruvate as a nucleophilic substrate
journal, January 2017

An Enantio- and Diastereoselective Chemoenzymatic Synthesis of α-Fluoro β-Hydroxy Carboxylic Esters
journal, April 2016

Evolution of Enzymatic Activities in the Enolase Superfamily: Characterization of the ( D )-Glucarate/Galactarate Catabolic Pathway in Escherichia coli ^†
journal, October 1998

Comparison of Two Metal-Dependent Pyruvate Aldolases Related by Convergent Evolution: Substrate Specificity, Kinetic Mechanism, and Substrate Channeling
journal, May 2010

Catalytic enantioselective aldol reactions
journal, January 2018

Recent Advances in Aldolase-Catalyzed Asymmetric Synthesis
journal, June 2007

Nucleophile Promiscuity of Engineered Class II Pyruvate Aldolase YfaU from E. Coli
journal, February 2018

Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions
journal, August 2014

Evaluation of fluoropyruvate as nucleophile in reactions catalysed by N-acetyl neuraminic acid lyase variants: scope, limitations and stereoselectivity
journal, January 2016

Crystal structures of the metal-dependent 2-dehydro-3-deoxy-galactarate aldolase suggest a novel reaction mechanism
journal, August 2000

Mechanism-based inhibition of an aldolase at high concentrations of its natural substrate acetaldehyde: structural insights and protective strategies
journal, January 2016

Engineered Fluorine Metabolism and Fluoropolymer Production in Living Cells
journal, September 2017

Aldolase-catalysed stereoselective synthesis of fluorinated small molecules
journal, April 2017

Organic fluorine compounds: a great opportunity for enhanced materials properties
journal, January 2011

2-Keto-3-Deoxy- l -Rhamnonate Aldolase (YfaU) as Catalyst in Aldol Additions of Pyruvate to Amino Aldehyde Derivatives
journal, May 2017

Structure and Mechanism of HpcH: A Metal Ion Dependent Class II Aldolase from the Homoprotocatechuate Degradation Pathway of Escherichia coli
journal, November 2007

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

Fluorine in Pharmaceuticals: Looking Beyond Intuition
journal, September 2007

Einführung von Fluor und fluorhaltigen funktionellen Gruppen
journal, July 2013

Expanding the Fluorine Chemistry of Living Systems Using Engineered Polyketide Synthase Pathways
journal, September 2013

Eukaryotic and Bacterial Gene Clusters Related to an Alternative Pathway of Nonphosphorylated L-Rhamnose Metabolism
journal, May 2008

Enantioselective Chemo- and Biocatalysis: Partners in Retrosynthesis
journal, June 2017

Enantioselective aldol reactions with masked fluoroacetates
journal, January 2016