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A reductive aminase from Aspergillus oryzae.

Aleku GA, France SP, Man H, Mangas-Sanchez J, Montgomery SL, Sharma M, Leipold F, Hussain S, Grogan G, Turner NJ
Nat Chem 9 961-969 (2017)
Cited: 77 times
EuropePMC logo PMID: 28937665

Abstract

Reductive amination is one of the most important methods for the synthesis of chiral amines. Here we report the discovery of an NADP(H)-dependent reductive aminase from Aspergillus oryzae (AspRedAm, Uniprot code Q2TW47) that can catalyse the reductive coupling of a broad set of carbonyl compounds with a variety of primary and secondary amines with up to >98% conversion and with up to >98% enantiomeric excess. In cases where both carbonyl and amine show high reactivity, it is possible to employ a 1:1 ratio of the substrates, forming amine products with up to 94% conversion. Steady-state kinetic studies establish that the enzyme is capable of catalysing imine formation as well as reduction. Crystal structures of AspRedAm in complex with NADP(H) and also with both NADP(H) and the pharmaceutical ingredient (R)-rasagiline are reported. We also demonstrate preparative scale reductive aminations with wild-type and Q240A variant biocatalysts displaying total turnover numbers of up to 32,000 and space time yields up to 3.73 g l-1 d-1.

Reviews - 5g6s mentioned but not cited (1)

  1. Redesigning Enzymes for Biocatalysis: Exploiting Structural Understanding for Improved Selectivity. Ding Y, Perez-Ortiz G, Peate J, Barry SM. Front Mol Biosci 9 908285 (2022)

Articles - 5g6s mentioned but not cited (3)

  1. Characterization of imine reductases in reductive amination for the exploration of structure-activity relationships. Montgomery SL, Pushpanath A, Heath RS, Marshall JR, Klemstein U, Galman JL, Woodlock D, Bisagni S, Taylor CJ, Mangas-Sanchez J, Ramsden JI, Dominguez B, Turner NJ. Sci Adv 6 eaay9320 (2020)
  2. Structural Characterization of an S-enantioselective Imine Reductase from Mycobacterium Smegmatis. Meyer T, Zumbrägel N, Geerds C, Gröger H, Niemann HH. Biomolecules 10 E1130 (2020)
  3. Engineering of Reductive Aminases for Asymmetric Synthesis of Enantiopure Rasagiline. Zhang K, He Y, Zhu J, Zhang Q, Tang L, Cui L, Feng Y. Front Bioeng Biotechnol 9 798147 (2021)


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  1. Biocatalysis: Enzymatic Synthesis for Industrial Applications. Wu S, Snajdrova R, Moore JC, Baldenius K, Bornscheuer UT. Angew Chem Int Ed Engl 60 88-119 (2021)
  2. Enzymatic Late-Stage Modifications: Better Late Than Never. Romero E, Jones BS, Hogg BN, Rué Casamajo A, Hayes MA, Flitsch SL, Turner NJ, Schnepel C. Angew Chem Int Ed Engl 60 16824-16855 (2021)
  3. Biocatalytic Reduction Reactions from a Chemist's Perspective. Hollmann F, Opperman DJ, Paul CE. Angew Chem Int Ed Engl 60 5644-5665 (2021)
  4. Recent advances in imine reductase-catalyzed reactions. Lenz M, Borlinghaus N, Weinmann L, Nestl BM. World J Microbiol Biotechnol 33 199 (2017)
  5. Enzymatic strategies for asymmetric synthesis. Hall M. RSC Chem Biol 2 958-989 (2021)
  6. Synthetic Enzyme-Catalyzed CO2 Fixation Reactions. Aleku GA, Roberts GW, Titchiner GR, Leys D. ChemSusChem 14 1781-1804 (2021)
  7. Metal-free multicomponent approach for the synthesis of propargylamine: a review. Ghosh S, Biswas K. RSC Adv 11 2047-2065 (2021)
  8. Reductive aminations by imine reductases: from milligrams to tons. Gilio AK, Thorpe TW, Turner N, Grogan G. Chem Sci 13 4697-4713 (2022)
  9. Unlocking New Reactivities in Enzymes by Iminium Catalysis. Xu G, Poelarends GJ. Angew Chem Int Ed Engl 61 e202203613 (2022)
  10. Enzymatic synthesis of fluorinated compounds. Cheng X, Ma L. Appl Microbiol Biotechnol 105 8033-8058 (2021)
  11. New Trends and Future Opportunities in the Enzymatic Formation of C-C, C-N, and C-O bonds. Sangster JJ, Marshall JR, Turner NJ, Mangas-Sanchez J. Chembiochem 23 e202100464 (2022)
  12. Recent Advances in Biocatalysis for Drug Synthesis. Kinner A, Nerke P, Siedentop R, Steinmetz T, Classen T, Rosenthal K, Nett M, Pietruszka J, Lütz S. Biomedicines 10 964 (2022)
  13. Hijacking Chemical Reactions of P450 Enzymes for Altered Chemical Reactions and Asymmetric Synthesis. Rajakumara E, Saniya D, Bajaj P, Rajeshwari R, Giri J, Davari MD. Int J Mol Sci 24 214 (2022)

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  1. Anti-Markovnikov alkene oxidation by metal-oxo-mediated enzyme catalysis. Hammer SC, Kubik G, Watkins E, Huang S, Minges H, Arnold FH. Science 358 215-218 (2017)
  2. Screening and characterization of a diverse panel of metagenomic imine reductases for biocatalytic reductive amination. Marshall JR, Yao P, Montgomery SL, Finnigan JD, Thorpe TW, Palmer RB, Mangas-Sanchez J, Duncan RAM, Heath RS, Graham KM, Cook DJ, Charnock SJ, Turner NJ. Nat Chem 13 140-148 (2021)
  3. Breaking Symmetry: Engineering Single-Chain Dimeric Streptavidin as Host for Artificial Metalloenzymes. Wu S, Zhou Y, Rebelein JG, Kuhn M, Mallin H, Zhao J, Igareta NV, Ward TR. J Am Chem Soc 141 15869-15878 (2019)
  4. Generation of amine dehydrogenases with increased catalytic performance and substrate scope from ε-deaminating L-Lysine dehydrogenase. Tseliou V, Knaus T, Masman MF, Corrado ML, Mutti FG. Nat Commun 10 3717 (2019)
  5. New imine-reducing enzymes from β-hydroxyacid dehydrogenases by single amino acid substitutions. Lenz M, Fademrecht S, Sharma M, Pleiss J, Grogan G, Nestl BM. Protein Eng Des Sel 31 109-120 (2018)
  6. Electrocatalytic Volleyball: Rapid Nanoconfined Nicotinamide Cycling for Organic Synthesis in Electrode Pores. Megarity CF, Siritanaratkul B, Heath RS, Wan L, Morello G, FitzPatrick SR, Booth RL, Sills AJ, Robertson AW, Warner JH, Turner NJ, Armstrong FA. Angew Chem Int Ed Engl 58 4948-4952 (2019)
  7. Asymmetric synthesis of primary amines catalyzed by thermotolerant fungal reductive aminases. Mangas-Sanchez J, Sharma M, Cosgrove SC, Ramsden JI, Marshall JR, Thorpe TW, Palmer RB, Grogan G, Turner NJ. Chem Sci 11 5052-5057 (2020)
  8. Fermentative Production of N-Alkylated Glycine Derivatives by Recombinant Corynebacterium glutamicum Using a Mutant of Imine Reductase DpkA From Pseudomonas putida. Mindt M, Hannibal S, Heuser M, Risse JM, Sasikumar K, Nampoothiri KM, Wendisch VF. Front Bioeng Biotechnol 7 232 (2019)
  9. Multifunctional biocatalyst for conjugate reduction and reductive amination. Thorpe TW, Marshall JR, Harawa V, Ruscoe RE, Cuetos A, Finnigan JD, Angelastro A, Heath RS, Parmeggiani F, Charnock SJ, Howard RM, Kumar R, Daniels DSB, Grogan G, Turner NJ. Nature 604 86-91 (2022)
  10. Terminal Alkenes from Acrylic Acid Derivatives via Non-Oxidative Enzymatic Decarboxylation by Ferulic Acid Decarboxylases. Aleku GA, Prause C, Bradshaw-Allen RT, Plasch K, Glueck SM, Bailey SS, Payne KAP, Parker DA, Faber K, Leys D. ChemCatChem 10 3736-3745 (2018)
  11. A biocatalytic cascade for the amination of unfunctionalised cycloalkanes. Tavanti M, Mangas-Sanchez J, Montgomery SL, Thompson MP, Turner NJ. Org Biomol Chem 15 9790-9793 (2017)
  12. Biocatalytic Routes to Enantiomerically Enriched Dibenz[c,e]azepines. France SP, Aleku GA, Sharma M, Mangas-Sanchez J, Howard RM, Steflik J, Kumar R, Adams RW, Slabu I, Crook R, Grogan G, Wallace TW, Turner NJ. Angew Chem Int Ed Engl 56 15589-15593 (2017)
  13. Enantioselective C-H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands. Dong Y, Lund CJ, Porter GJ, Clarke RM, Zheng SL, Cundari TR, Betley TA. J Am Chem Soc 143 817-829 (2021)
  14. Biocatalytic Production of Amino Carbohydrates through Oxidoreductase and Transaminase Cascades. Aumala V, Mollerup F, Jurak E, Blume F, Karppi J, Koistinen AE, Schuiten E, Voß M, Bornscheuer U, Deska J, Master ER. ChemSusChem 12 848-857 (2019)
  15. Biocatalytic Synthesis of Chiral N-Functionalized Amino Acids. Hyslop JF, Lovelock SL, Sutton PW, Brown KK, Watson AJB, Roiban GD. Angew Chem Int Ed Engl 57 13821-13824 (2018)
  16. One-Pot Synthesis of Chiral N-Arylamines by Combining Biocatalytic Aminations with Buchwald-Hartwig N-Arylation. Cosgrove SC, Thompson MP, Ahmed ST, Parmeggiani F, Turner NJ. Angew Chem Int Ed Engl 59 18156-18160 (2020)
  17. Asymmetric Synthesis of N-Substituted α-Amino Esters from α-Ketoesters via Imine Reductase-Catalyzed Reductive Amination. Yao P, Marshall JR, Xu Z, Lim J, Charnock SJ, Zhu D, Turner NJ. Angew Chem Int Ed Engl 60 8717-8721 (2021)
  18. Mechanistic Insight into the Catalytic Promiscuity of Amine Dehydrogenases: Asymmetric Synthesis of Secondary and Primary Amines. Tseliou V, Masman MF, Böhmer W, Knaus T, Mutti FG. Chembiochem 20 800-812 (2019)
  19. Rapid Screening of Diverse Biotransformations for Enzyme Evolution. Kempa EE, Galman JL, Parmeggiani F, Marshall JR, Malassis J, Fontenelle CQ, Vendeville JB, Linclau B, Charnock SJ, Flitsch SL, Turner NJ, Barran PE. JACS Au 1 508-516 (2021)
  20. Using enzymes to tame nitrogen-centred radicals for enantioselective hydroamination. Ye Y, Cao J, Oblinsky DG, Verma D, Prier CK, Scholes GD, Hyster TK. Nat Chem 15 206-212 (2023)
  21. A unique fungal strain collection from Vietnam characterized for high performance degraders of bioecological important biopolymers and lipids. Brandt SC, Ellinger B, van Nguyen T, Thi QD, van Nguyen G, Baschien C, Yurkov A, Hahnke RL, Schäfer W, Gand M. PLoS One 13 e0202695 (2018)
  22. Electrochemically driven C-N bond formation from CO2 and ammonia at the triple-phase boundary. Li J, Kornienko N. Chem Sci 13 3957-3964 (2022)
  23. Enhancing cofactor recycling in the bioconversion of racemic alcohols to chiral amines with alcohol dehydrogenase and amine dehydrogenase by coupling cells and cell-free system. Liu J, Li Z. Biotechnol Bioeng 116 536-542 (2019)
  24. Expanding the Toolbox of R-Selective Amine Transaminases by Identification and Characterization of New Members. Telzerow A, Paris J, Håkansson M, González-Sabín J, Ríos-Lombardía N, Gröger H, Morís F, Schürmann M, Schwab H, Steiner K. Chembiochem 22 1232-1242 (2021)
  25. Reductive amination of ketones catalyzed by whole cell biocatalysts containing imine reductases (IREDs). Maugeri Z, Rother D. J Biotechnol 258 167-170 (2017)
  26. Synthesis of Stereoenriched Piperidines via Chemo-Enzymatic Dearomatization of Activated Pyridines. Harawa V, Thorpe TW, Marshall JR, Sangster JJ, Gilio AK, Pirvu L, Heath RS, Angelastro A, Finnigan JD, Charnock SJ, Nafie JW, Grogan G, Whitehead RC, Turner NJ. J Am Chem Soc 144 21088-21095 (2022)
  27. A Dual Anchoring Strategy for the Directed Evolution of Improved Artificial Transfer Hydrogenases Based on Carbonic Anhydrase. Stein A, Chen D, Igareta NV, Cotelle Y, Rebelein JG, Ward TR. ACS Cent Sci 7 1874-1884 (2021)
  28. Characterization of a Putrescine Transaminase From Pseudomonas putida and its Application to the Synthesis of Benzylamine Derivatives. Galman JL, Gahloth D, Parmeggiani F, Slabu I, Leys D, Turner NJ. Front Bioeng Biotechnol 6 205 (2018)
  29. Enantioselective reduction of sulfur-containing cyclic imines through biocatalysis. Zumbrägel N, Merten C, Huber SM, Gröger H. Nat Commun 9 1949 (2018)
  30. Secondary amines as coupling partners in direct catalytic asymmetric reductive amination. Wu Z, Du S, Gao G, Yang W, Yang X, Huang H, Chang M. Chem Sci 10 4509-4514 (2019)
  31. Biomimetic synthesis of 2-substituted N-heterocycle alkaloids by one-pot hydrolysis, transamination and decarboxylative Mannich reaction. Galman JL, Slabu I, Parmeggiani F, Turner NJ. Chem Commun (Camb) 54 11316-11319 (2018)
  32. Crossing the Border: From Keto- to Imine Reduction in Short-Chain Dehydrogenases/Reductases. Roth S, Stockinger P, Steff J, Steimle S, Sautner V, Tittmann K, Pleiss J, Müller M. Chembiochem 21 2615-2619 (2020)
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  37. Kinetic Resolution of Racemic Primary Amines Using Geobacillus stearothermophilus Amine Dehydrogenase Variant. Tseliou V, Knaus T, Vilím J, Masman MF, Mutti FG. ChemCatChem 12 2184-2188 (2020)
  38. The combination of asymmetric hydrogenation of olefins and direct reductive amination. Yuan S, Gao G, Wang L, Liu C, Wan L, Huang H, Geng H, Chang M. Nat Commun 11 621 (2020)
  39. A Reductive Aminase Switches to Imine Reductase Mode for a Bulky Amine Substrate. Gilio AK, Thorpe TW, Heyam A, Petchey MR, Pogrányi B, France SP, Howard RM, Karmilowicz MJ, Lewis R, Turner N, Grogan G. ACS Catal 13 1669-1677 (2023)
  40. Genome mining and characterisation of a novel transaminase with remote stereoselectivity. Gavin DP, Reen FJ, Rocha-Martin J, Abreu-Castilla I, Woods DF, Foley AM, Sánchez-Murcia PA, Schwarz M, O'Neill P, Maguire AR, O'Gara F. Sci Rep 9 20285 (2019)
  41. Improving the Thermostability and Activity of Transaminase From Aspergillus terreus by Charge-Charge Interaction. Cao JR, Fan FF, Lv CJ, Wang HP, Li Y, Hu S, Zhao WR, Chen HB, Huang J, Mei LH. Front Chem 9 664156 (2021)
  42. Metagenomic discovery of a novel transaminase for valorization of monoaromatic compounds. Pawar SV, Hallam SJ, Yadav VG. RSC Adv 8 22490-22497 (2018)
  43. Reshaping the substrate binding region of (R)-selective ω-transaminase for asymmetric synthesis of (R)-3-amino-1-butanol. Gao X, Zhang X, Zhu N, Mou Y, Zhang H, Liu X, Wei P. Appl Microbiol Biotechnol 104 3959-3969 (2020)
  44. Actinomycetes-derived imine reductases with a preference towards bulky amine substrates. Zhang J, Li X, Chen R, Tan X, Liu X, Ma Y, Zhu F, An C, Wei G, Yao Y, Yang L, Zhang P, Wu Q, Sun Z, Wang BG, Gao SS, Cui C. Commun Chem 5 123 (2022)
  45. Enantioselective Single and Dual α-C-H Bond Functionalization of Cyclic Amines via Enzymatic Carbene Transfer. Ren X, Couture BM, Liu N, Lall MS, Kohrt JT, Fasan R. J Am Chem Soc 145 537-550 (2023)
  46. Engineering Promiscuous Alcohol Dehydrogenase Activity of a Reductive Aminase AspRedAm for Selective Reduction of Biobased Furans. Jia HY, Yang ZY, Chen Q, Zong MH, Li N. Front Chem 9 610091 (2021)
  47. Structure and Mutation of the Native Amine Dehydrogenase MATOUAmDH2. Bennett M, Ducrot L, Vergne-Vaxelaire C, Grogan G. Chembiochem 23 e202200136 (2022)
  48. Three-Component Stereoselective Enzymatic Synthesis of Amino-Diols and Amino-Polyols. Ford GJ, Swanson CR, Bradshaw Allen RT, Marshall JR, Mattey AP, Turner NJ, Clapés P, Flitsch SL. JACS Au 2 2251-2258 (2022)
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  53. Hot off the press. Hill RA, Sutherland A. Nat Prod Rep 34 1340-1344 (2017)
  54. Imine reduction by an Ornithine cyclodeaminase/μ-crystallin homolog purified from Candida parapsilosis ATCC 7330. Uma Mahesh VNM, Chadha A. Biotechnol Rep (Amst) 31 e00664 (2021)
  55. Novel Kinetic Resolution of Thiazolo-Benzimidazolines Using MAO Enzymes. Villamil V, Vairoletti F, Tijman A, López G, Peixoto de Abreu Lima A, Saiz C, Iglesias C, Mahler G. ACS Omega 8 42114-42125 (2023)
  56. One-Pot Biocatalytic Synthesis of Primary, Secondary, and Tertiary Amines with Two Stereocenters from α,β-Unsaturated Ketones Using Alkyl-Ammonium Formate. Knaus T, Corrado ML, Mutti FG. ACS Catal 12 14459-14475 (2022)
  57. Structure of the imine reductase from Ajellomyces dermatitidis in three crystal forms. Sharma M, Cuetos A, Willliams A, González-Martínez D, Grogan G. Acta Crystallogr F Struct Biol Commun 79 224-230 (2023)
  58. Structure-Based Design of Small Imine Reductase Panels for Target Substrates. Yu Y, Rué Casamajo A, Finnigan W, Schnepel C, Barker R, Morrill C, Heath RS, De Maria L, Turner NJ, Scrutton NS. ACS Catal 13 12310-12321 (2023)
  59. Structure-guided semi-rational design of an imine reductase for enantio-complementary synthesis of pyrrolidinamine. Zhang J, Ma Y, Zhu F, Bao J, Wu Q, Gao SS, Cui C. Chem Sci 14 4265-4272 (2023)
  60. The Discovery of Imine Reductases and their Utilisation for the Synthesis of Tetrahydroisoquinolines. Cárdenas-Fernández M, Roddan R, Carter EM, Hailes HC, Ward JM. ChemCatChem 15 e202201126 (2023)


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