Biocatalytic synthesis of non-standard amino acids by a decarboxylative aldol reaction

Ellis, Jonathan M.; Campbell, Meghan E.; Kumar, Prasanth; Geunes, Eric P.; Bingman, Craig A.; Buller, Andrew R.

doi:10.1038/s41929-022-00743-0

Biocatalytic synthesis of non-standard amino acids by a decarboxylative aldol reaction

Journal Article · 01 February 2022 · Nat. Catalysis

DOI:https://doi.org/10.1038/s41929-022-00743-0· OSTI ID:1855464

Ellis, Jonathan M.; Campbell, Meghan E.; Kumar, Prasanth; Geunes, Eric P.; Bingman, Craig A.; Buller, Andrew R.

Research Organization:: Advanced Photon Source (APS), Argonne National Laboratory (ANL), Argonne, IL (US)

Sponsoring Organization:: DOE - Office Of Science; NIH

OSTI ID:: 1855464

Journal Information:: Nat. Catalysis, Journal Name: Nat. Catalysis Vol. 5

Country of Publication:: United States

Language:: ENGLISH

References (40)

Iterative Saturation Mutagenesis Accelerates Laboratory Evolution of Enzyme Stereoselectivity: Rigorous Comparison with Traditional Methods Reetz, Manfred T.; Prasad, Shreenath; Carballeira, José D. Journal of the American Chemical Society, Vol. 132, Issue 26 https://doi.org/10.1021/ja1030479	journal	June 2010
The I-TASSER Suite: protein structure and function prediction Yang, Jianyi; Yan, Renxiang; Roy, Ambrish Nature Methods, Vol. 12, Issue 1 https://doi.org/10.1038/nmeth.3213	journal	December 2014
Biocatalytic Methods for CC Bond Formation Fesko, Kateryna; Gruber-Khadjawi, Mandana ChemCatChem, Vol. 5, Issue 6 https://doi.org/10.1002/cctc.201200709	journal	February 2013
Combining Aldolases and Transaminases for the Synthesis of 2-Amino-4-hydroxybutanoic Acid Hernandez, Karel; Bujons, Jordi; Joglar, Jesús ACS Catalysis, Vol. 7, Issue 3 https://doi.org/10.1021/acscatal.6b03181	journal	February 2017
Heterologous expression systems for polyketide synthases Fujii, Isao Nat. Prod. Rep., Vol. 26, Issue 2 https://doi.org/10.1039/B817092B	journal	January 2009
On the catalytic mechanism and stereospecificity of Escherichia coli l -threonine aldolase di Salvo, Martino L.; Remesh, Soumya G.; Vivoli, Mirella FEBS Journal, Vol. 281, Issue 1 https://doi.org/10.1111/febs.12581	journal	November 2013
New Generation of Biocatalysts for Organic Synthesis Nestl, Bettina M.; Hammer, Stephan C.; Nebel, Bernd A. Angewandte Chemie International Edition, Vol. 53, Issue 12 https://doi.org/10.1002/anie.201302195	journal	February 2014
Preparation of β-hydroxy-α-amino Acid Using Recombinant d -Threonine Aldolase Goldberg, Steven L.; Goswami, Animesh; Guo, Zhiwei Organic Process Research & Development, Vol. 19, Issue 9 https://doi.org/10.1021/acs.oprd.5b00191	journal	August 2015
Pyridoxal Phosphate Enzymes: Mechanistic, Structural, and Evolutionary Considerations Eliot, Andrew C.; Kirsch, Jack F. Annual Review of Biochemistry, Vol. 73, Issue 1 https://doi.org/10.1146/annurev.biochem.73.011303.074021	journal	June 2004
Engineered Biosynthesis of β-Alkyl Tryptophan Analogues Boville, Christina E.; Scheele, Remkes A.; Koch, Philipp Angewandte Chemie International Edition, Vol. 57, Issue 45 https://doi.org/10.1002/anie.201807998	journal	October 2018
An efficient and concise entry to (-)-4,5-dihydroxy----norvaline. Formal synthesis of clavalanine. Ariza, Jesus; Font, Josep; Ortuño, Rosa M. Tetrahedron Letters, Vol. 32, Issue 17 https://doi.org/10.1016/0040-4039(91)85018-Z	journal	April 1991
Crystallization-induced asymmetric transformations (CIAT): stereoconvergent acid-catalyzed lactonization of substituted 2-amino-4-aryl-4-hydroxybutanoic acids Berkeš, Dušan; Kolarovič, Andrej; Manduch, Robert Tetrahedron: Asymmetry, Vol. 16, Issue 11 https://doi.org/10.1016/j.tetasy.2005.04.024	journal	June 2005
Design of an in vitro biocatalytic cascade for the manufacture of islatravir Huffman, Mark A.; Fryszkowska, Anna; Alvizo, Oscar Science, Vol. 366, Issue 6470 https://doi.org/10.1126/science.aay8484	journal	December 2019
Proline and hydroxyproline metabolism: implications for animal and human nutrition Wu, Guoyao; Bazer, Fuller W.; Burghardt, Robert C. Amino Acids, Vol. 40, Issue 4 https://doi.org/10.1007/s00726-010-0715-z	journal	August 2010
Nitroalkanes as Versatile Nucleophiles for Enzymatic Synthesis of Noncanonical Amino Acids Romney, David K.; Sarai, Nicholas S.; Arnold, Frances H. ACS Catalysis, Vol. 9, Issue 9 https://doi.org/10.1021/acscatal.9b02089	journal	August 2019
Enzymatic assembly of DNA molecules up to several hundred kilobases Gibson, Daniel G.; Young, Lei; Chuang, Ray-Yuan Nature Methods, Vol. 6, Issue 5, p. 343-345 https://doi.org/10.1038/nmeth.1318	journal	April 2009
Overcoming Thermodynamic and Kinetic Limitations of Aldolase-Catalyzed Reactions by Applying Multienzymatic Dynamic Kinetic Asymmetric Transformations Steinreiber, Johannes; Schürmann, Martin; Wolberg, Michael Angewandte Chemie International Edition, Vol. 46, Issue 10 https://doi.org/10.1002/anie.200604142	journal	February 2007
Divergent synthesis of complex diterpenes through a hybrid oxidative approach Zhang, Xiao; King-Smith, Emma; Dong, Liao-Bin Science, Vol. 369, Issue 6505 https://doi.org/10.1126/science.abb8271	journal	August 2020
Observation of Covalent Intermediates in an Enzyme Mechanism at Atomic Resolution Heine, A. Science, Vol. 294, Issue 5541 https://doi.org/10.1126/science.1063601	journal	October 2001
Recent advances in whole cell biocatalysis techniques bridging from investigative to industrial scale Wachtmeister, Jochen; Rother, Dörte Current Opinion in Biotechnology, Vol. 42 https://doi.org/10.1016/j.copbio.2016.05.005	journal	December 2016
Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?: Miniperspective Brown, Dean G.; Boström, Jonas Journal of Medicinal Chemistry, Vol. 59, Issue 10 https://doi.org/10.1021/acs.jmedchem.5b01409	journal	December 2015
Directed molecular evolution by machine learning and the influence of nonlinear interactions Fox, Richard Journal of Theoretical Biology, Vol. 234, Issue 2 https://doi.org/10.1016/j.jtbi.2004.11.031	journal	May 2005
Unlocking Reactivity of TrpB: A General Biocatalytic Platform for Synthesis of Tryptophan Analogues Romney, David K.; Murciano-Calles, Javier; Wehrmüller, Jöri E. Journal of the American Chemical Society, Vol. 139, Issue 31 https://doi.org/10.1021/jacs.7b05007	journal	July 2017
Building Bridges: Biocatalytic C–C-Bond Formation toward Multifunctional Products Schmidt, Nina G.; Eger, Elisabeth; Kroutil, Wolfgang ACS Catalysis, Vol. 6, Issue 7 https://doi.org/10.1021/acscatal.6b00758	journal	June 2016
Ro 22-5417, a new clavam antibiotic from Streptomyces clavuligerus. III. Absolute stereochemistry. MÜLler, Jean-Claude; Toome, Voldemar; Pruess, David L. The Journal of Antibiotics, Vol. 36, Issue 3 https://doi.org/10.7164/antibiotics.36.217	journal	January 1983
Upgrading aminoacyl-tRNA synthetases for genetic code expansion Vargas-Rodriguez, Oscar; Sevostyanova, Anastasia; Söll, Dieter Current Opinion in Chemical Biology, Vol. 46 https://doi.org/10.1016/j.cbpa.2018.07.014	journal	October 2018
Discovery of a pathway for terminal-alkyne amino acid biosynthesis Marchand, J. A.; Neugebauer, M. E.; Ing, M. C. Nature, Vol. 567, Issue 7748 https://doi.org/10.1038/s41586-019-1020-y	journal	March 2019
Separating Thermodynamics from Kinetics-A New Understanding of the Transketolase Reaction Marsden, Stefan R.; Gjonaj, Lorina; Eustace, Stephen J. ChemCatChem, Vol. 9, Issue 10 https://doi.org/10.1002/cctc.201601649	journal	April 2017
Broadening the scope of biocatalytic C–C bond formation Zetzsche, Lara E.; Narayan, Alison R. H. Nature Reviews Chemistry, Vol. 4, Issue 7 https://doi.org/10.1038/s41570-020-0191-2	journal	June 2020
Chemomimetic Biocatalysis: Exploiting the Synthetic Potential of Cofactor-Dependent Enzymes To Create New Catalysts Prier, Christopher K.; Arnold, Frances H. Journal of the American Chemical Society, Vol. 137, Issue 44 https://doi.org/10.1021/jacs.5b09348	journal	November 2015
Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition–Transamination Reactions Moreno, Carlos J.; Hernández, Karel; Charnok, Simon J. ACS Catalysis, Vol. 11, Issue 8 https://doi.org/10.1021/acscatal.1c00210	journal	April 2021
Expanding the Range of Substrate Acceptance of Enzymes: Combinatorial Active-Site Saturation Test Reetz, Manfred T.; Bocola, Marco; Carballeira, José Daniel Angewandte Chemie International Edition, Vol. 44, Issue 27 https://doi.org/10.1002/anie.200500767	journal	July 2005
Improved Cyclopropanation Activity of Histidine-Ligated Cytochrome P450 Enables the Enantioselective Formal Synthesis of Levomilnacipran Wang, Z. Jane; Renata, Hans; Peck, Nicole E. Angewandte Chemie International Edition, Vol. 53, Issue 26 https://doi.org/10.1002/anie.201402809	journal	May 2014
On the taught new tricks of enzymes immobilization: An all-inclusive overview Wahab, Roswanira Abdul; Elias, Nursyafiqah; Abdullah, Faizuan Reactive and Functional Polymers, Vol. 152 https://doi.org/10.1016/j.reactfunctpolym.2020.104613	journal	July 2020
l -Threonine Transaldolase Activity Is Enabled by a Persistent Catalytic Intermediate Kumar, Prasanth; Meza, Anthony; Ellis, Jonathan M. ACS Chemical Biology, Vol. 16, Issue 1 https://doi.org/10.1021/acschembio.0c00753	journal	December 2020
Exploring protein fitness landscapes by directed evolution Romero, Philip A.; Arnold, Frances H. Nature Reviews Molecular Cell Biology, Vol. 10, Issue 12 https://doi.org/10.1038/nrm2805	journal	December 2009
Crystal Structure of Human Maspin, a Serpin with Antitumor Properties Al-Ayyoubi, Maher; Gettins, Peter G. W.; Volz, Karl Journal of Biological Chemistry, Vol. 279, Issue 53 https://doi.org/10.1074/jbc.M409957200	journal	December 2004
Determination ofD-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene Marfey, Peter Carlsberg Research Communications, Vol. 49, Issue 6 https://doi.org/10.1007/BF02908688	journal	January 1984
Unusual Amino Acids in Medicinal Chemistry Blaskovich, Mark A. T. Journal of Medicinal Chemistry, Vol. 59, Issue 24 https://doi.org/10.1021/acs.jmedchem.6b00319	journal	September 2016
Unveiling the Biosynthetic Pathway of the Ribosomally Synthesized and Post-translationally Modified Peptide Ustiloxin B in Filamentous Fungi Ye, Ying; Minami, Atsushi; Igarashi, Yuya Angewandte Chemie International Edition, Vol. 55, Issue 28 https://doi.org/10.1002/anie.201602611	journal	May 2016

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