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Currently, synthetic methods for the trans-reduction of alkynes to E-alkenes remain limited, particularly in the realm of biocatalysis. Herein, we report the repurposing of a nonheme iron dioxygenase for the trans-reduction of alkynes. Through screening and directed evolution, we obtained variants of gentisate 1,2-dioxygenase that enable the preparation of structurally diverse E-alkenes in high yields (up to 99% yield) with excellent stereoselectivity (16 examples with E\/Z ratios of 99\/1) and chemoselectivity (21 cases with 0% alkane). Mechanistic studies suggest a pathway involving hydride attack to generate a trans anion intermediate, followed by protonation to directly furnish the E-alkene. This metalloenzymatic trans-reduction pathway is mechanistically distinct from the classical syn-addition\/isomerization pathway typically observed in transition-metal catalysis.<\/jats:p>","DOI":"10.1021\/jacs.6c13787","type":"journal-article","created":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T15:02:49Z","timestamp":1791212569000},"page":"42883-42889","source":"Crossref","is-referenced-by-count":0,"title":["Chemo- and Stereoselective\nSemireduction of Alkynes\nto\n                    <i>E<\/i>\n                    -Alkenes Catalyzed by Nonheme Iron Enzymes"],"prefix":"10.1021","volume":"148","author":[{"given":"Zicong","family":"Wan","sequence":"first","affiliation":[{"name":"Zhejiang University , , ,","place":["Hangzhou, China, 310058"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenxuan","family":"Zhang","sequence":"additional","affiliation":[{"name":"Zhejiang University , , ,","place":["Hangzhou, China, 310058"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yang","family":"Sun","sequence":"additional","affiliation":[{"name":"Zhejiang University , , ,","place":["Hangzhou, China, 310058"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hangwen","family":"Zheng","sequence":"additional","affiliation":[{"name":"Zhejiang University , , ,","place":["Hangzhou, China, 310058"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chang","family":"Ge","sequence":"additional","affiliation":[{"name":"Zhejiang University , , ,","place":["Hangzhou, China, 310058"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Beiyao","family":"Fu","sequence":"additional","affiliation":[{"name":"Zhejiang University , , ,","place":["Hangzhou, China, 310058"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8109-7929","authenticated-orcid":true,"given":"Pengfei","family":"Ji","sequence":"additional","affiliation":[{"name":"Zhejiang University , , ,","place":["Hangzhou, China, 310058"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,5]]},"reference":[{"issue":"8","key":"2026101414070450800_cit1","doi-asserted-by":"publisher","first-page":"2636","DOI":"10.1002\/anie.201507151","article-title":"Catalytic Enantioselective Functionalization of Unactivated\nTerminal Alkenes","volume":"55","author":"Coombs","year":"2016","journal-title":"Angew. Chem., Int. Ed."},{"issue":"7","key":"2026101414070450800_cit2","doi-asserted-by":"publisher","first-page":"883","DOI":"10.1039\/C8CC07828A","article-title":"Biocatalytic selective functionalisation\nof alkenes via single-step and one-pot multi-step reactions","volume":"55","author":"Wu","year":"2019","journal-title":"Chem. Commun."},{"issue":"52","key":"2026101414070450800_cit3","doi-asserted-by":"publisher","first-page":"15642","DOI":"10.1002\/anie.201507152","article-title":"Catalytic,\nStereoselective Dihalogenation\nof Alkenes: Challenges and Opportunities","volume":"54","author":"Cresswell","year":"2015","journal-title":"Angew.\nChem., Int. Ed."},{"issue":"8","key":"2026101414070450800_cit4","doi-asserted-by":"publisher","first-page":"2504","DOI":"10.1039\/C9CS00138G","article-title":"Enantioconvergent\nand enantiodivergent catalytic hydrogenation of isomeric olefins","volume":"49","author":"Massaro","year":"2020","journal-title":"Chem. Soc. Rev."},{"issue":"18","key":"2026101414070450800_cit5","doi-asserted-by":"publisher","first-page":"2426","DOI":"10.1021\/acs.accounts.3c00341","article-title":"Taking Olefin\nMetathesis to the Limit: Stereocontrolled Synthesis of Trisubstituted\nAlkenes","volume":"56","author":"Hoveyda","year":"2023","journal-title":"Acc. Chem. Res."},{"issue":"2","key":"2026101414070450800_cit6","doi-asserted-by":"publisher","first-page":"409","DOI":"10.1021\/cs400992z","article-title":"Enantioselective trans-Dihydroxylation\nof Aryl Olefins by Cascade Biocatalysis with Recombinant Escherichia\ncoli Coexpressing Monooxygenase and Epoxide Hydrolase","volume":"4","author":"Wu","year":"2014","journal-title":"ACS Catal."},{"issue":"26","key":"2026101414070450800_cit7","doi-asserted-by":"publisher","first-page":"5409","DOI":"10.1021\/ol7019185","article-title":"Stereocomplementary Bioreduction\nof \u03b1,\u03b2-Unsaturated Dicarboxylic Acids and Dimethyl Esters\nusing Enoate Reductases: Enzyme- and Substrate-Based Stereocontrol","volume":"9","author":"Stueckler","year":"2007","journal-title":"Org. 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Lett."},{"issue":"42","key":"2026101414070450800_cit11","doi-asserted-by":"publisher","first-page":"13452","DOI":"10.1021\/jacs.5b07521","article-title":"One-step Synthesis\nof Core-Gold\/Shell-Ceria Nanomaterial\nand Its Catalysis for Highly Selective Semihydrogenation of Alkynes","volume":"137","author":"Mitsudome","year":"2015","journal-title":"J. Am. Chem. Soc."},{"issue":"40","key":"2026101414070450800_cit12","doi-asserted-by":"publisher","first-page":"12214","DOI":"10.1002\/chem.201001143","article-title":"A Selective\nRu-Catalyzed Semireduction\nof Alkynes to Z Olefins under Transfer-Hydrogenation Conditions","volume":"16","author":"Belger","year":"2010","journal-title":"Chem. \u2013 Eur. 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Catal."},{"issue":"39","key":"2026101414070450800_cit16","doi-asserted-by":"publisher","first-page":"5372","DOI":"10.1039\/C7CC02140B","article-title":"Ligand-free nickel-catalyzed\nsemihydrogenation of alkynes with sodium borohydride: a highly efficient\nand selective process for cis-alkenes under ambient conditions","volume":"53","author":"Wen","year":"2017","journal-title":"Chem. Commun."},{"issue":"9","key":"2026101414070450800_cit17","doi-asserted-by":"publisher","first-page":"4397","DOI":"10.1021\/acs.chemrev.4c00001","article-title":"Renaissance in Alkyne\nSemihydrogenation: Mechanism, Selectivity,\nFunctional Group Tolerance, and Applications in Organic Synthesis","volume":"125","author":"Kusy","year":"2025","journal-title":"Chem. 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Rev."},{"issue":"8019","key":"2026101414070450800_cit26","doi-asserted-by":"publisher","first-page":"37","DOI":"10.1038\/s41586-024-07506-w","article-title":"Expanding chemistry through in vitro and in vivo biocatalysis","volume":"631","author":"Kissman","year":"2024","journal-title":"Nature"},{"issue":"9","key":"2026101414070450800_cit27","doi-asserted-by":"publisher","first-page":"1446","DOI":"10.1021\/acs.accounts.4c00129","article-title":"From Ground-State\nto Excited-State Activation Modes:\nFlavin-Dependent \u201cEne\u201d-Reductases Catalyzed Non-natural\nRadical Reactions","volume":"57","author":"Fu","year":"2024","journal-title":"Acc. Chem. Res."},{"issue":"5","key":"2026101414070450800_cit28","doi-asserted-by":"publisher","first-page":"1209","DOI":"10.1021\/acs.accounts.0c00591","article-title":"Navigating the Unnatural Reaction Space: Directed Evolution\nof Heme Proteins for Selective Carbene and Nitrene Transfer","volume":"54","author":"Yang","year":"2021","journal-title":"Acc. Chem. Res."},{"issue":"7","key":"2026101414070450800_cit29","doi-asserted-by":"publisher","first-page":"4135","DOI":"10.1021\/acs.chemrev.5c00837","article-title":"Metalloenzyme-Catalyzed\nRadical Reactions\nUnknown or Uncommon in Native Enzymology","volume":"126","author":"Fu","year":"2026","journal-title":"Chem.\nRev."},{"issue":"1","key":"2026101414070450800_cit30","doi-asserted-by":"publisher","first-page":"74","DOI":"10.1038\/s41557-024-01671-1","article-title":"Unmasking the reverse catalytic activity\nof \u2018ene\u2019-reductases\nfor asymmetric carbonyl desaturation","volume":"17","author":"Wang","year":"2025","journal-title":"Nat. Chem."},{"issue":"19","key":"2026101414070450800_cit31","doi-asserted-by":"publisher","first-page":"10877","DOI":"10.1021\/acs.chemrev.4c00136","article-title":"Noncanonical Amino Acids: Bringing\nNew-to-Nature Functionalities to Biocatalysis","volume":"124","author":"Brouwer","year":"2024","journal-title":"Chem. Rev."},{"issue":"8090","key":"2026101414070450800_cit32","doi-asserted-by":"publisher","first-page":"648","DOI":"10.1038\/s41586-025-09738-w","article-title":"Synthesis\nof\nenantioenriched atropisomers by biocatalytic deracemization","volume":"647","author":"Roos","year":"2025","journal-title":"Nature"},{"issue":"6784","key":"2026101414070450800_cit33","doi-asserted-by":"publisher","first-page":"eadw3365","DOI":"10.1126\/science.adw3365","article-title":"Engineered aldehyde\ndehydrogenases for amide bond formation","volume":"391","author":"Gao","year":"2026","journal-title":"Science"},{"issue":"9","key":"2026101414070450800_cit34","doi-asserted-by":"publisher","first-page":"9709","DOI":"10.1021\/jacs.5c20979","article-title":"Pyridoxal 5\u2032-Phosphate-Dependent\nEnzymatic Decarboxylative\nAnnulation","volume":"148","author":"Chai","year":"2026","journal-title":"J. Am. Chem. Soc."},{"issue":"50","key":"2026101414070450800_cit35","doi-asserted-by":"publisher","first-page":"19585","DOI":"10.1021\/jacs.9b11608","article-title":"Nitrene Transfer\nCatalyzed by a Non-Heme Iron Enzyme and Enhanced by Non-Native Small-Molecule\nLigands","volume":"141","author":"Goldberg","year":"2019","journal-title":"J. Am. Chem. 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Synth."},{"issue":"8","key":"2026101414070450800_cit38","doi-asserted-by":"publisher","first-page":"967","DOI":"10.1038\/s44160-024-00536-2","article-title":"Biocatalytic\nenantioselective C(sp3)\u2013H fluorination enabled by directed\nevolution of non-haem iron enzymes","volume":"3","author":"Zhao","year":"2024","journal-title":"Nat. Synth."},{"issue":"29","key":"2026101414070450800_cit39","doi-asserted-by":"publisher","first-page":"31063","DOI":"10.1021\/jacs.6c06323","article-title":"Influence\nof Primary Coordination Sphere on Anion Rebound Selectivity in Nonheme\nFe Enzyme-Catalyzed C(sp3)\u2013H Functionalization: A Comparative\nExperimental and Computational Study of EgtB and ACCO","volume":"148","author":"Zhao","year":"2026","journal-title":"J. Am. Chem. Soc."},{"issue":"50","key":"2026101414070450800_cit40","doi-asserted-by":"publisher","first-page":"34878","DOI":"10.1021\/jacs.4c14310","article-title":"Biocatalytic\nGeneration of Trifluoromethyl Radicals by Nonheme Iron Enzymes for\nEnantioselective Alkene Difunctionalization","volume":"146","author":"Zhang","year":"2024","journal-title":"J. Am. Chem. Soc."},{"issue":"9","key":"2026101414070450800_cit41","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202423507","article-title":"Enantioselective\nTrifluoromethylazidation of Styrenyl Olefins Catalyzed by an Engineered\nNonheme Iron Enzyme","volume":"64","author":"He","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"issue":"11","key":"2026101414070450800_cit42","doi-asserted-by":"publisher","first-page":"1773","DOI":"10.1038\/s41589-025-01953-w","article-title":"Nonheme Fe 1,3-nitrogen migratases for asymmetric noncanonical amino\nacid synthesis","volume":"21","author":"Zhao","year":"2025","journal-title":"Nat. Chem. Biol."},{"issue":"48","key":"2026101414070450800_cit43","doi-asserted-by":"publisher","first-page":"44041","DOI":"10.1021\/jacs.5c11008","article-title":"Biocatalytic Synthesis of N-Protected\n\u03b1-Amino Acids through 1,3-Nitrogen Migration by Nonheme Iron\nEnzymes","volume":"147","author":"Yuan","year":"2025","journal-title":"J. Am. Chem. Soc."},{"issue":"30","key":"2026101414070450800_cit44","doi-asserted-by":"publisher","first-page":"32384","DOI":"10.1021\/jacs.6c08775","article-title":"Directed Evolution\nof Nonheme Fe Enzymes for Enantioselective\nand Regiodivergent 1,3- and 1,4-Nitrogen Migration: Biocatalytic Asymmetric\nSynthesis of Noncanonical \u03b1- and \u03b2-Amino Acids","volume":"148","author":"Liu","year":"2026","journal-title":"J. Am. Chem. Soc."},{"issue":"6","key":"2026101414070450800_cit45","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202524718","article-title":"Nonheme Fe\nEnzyme-Catalyzed\nEnantiodivergent Nitrogen Migration: Directed Evolution and Computational\nStudy of Isopenicillin N Synthases for Biocatalytic Synthesis of Arylglycines","volume":"65","author":"Lin","year":"2026","journal-title":"Angew. Chem., Int. Ed."},{"issue":"39","key":"2026101414070450800_cit46","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202410283","article-title":"BioLindlar Catalyst: Ene-Reductase-Promoted Selective\nBioreduction of Cyanoalkynes to Give (Z)-Cyanoalkenes","volume":"63","author":"Gonza\u0301lez-Rodri\u0301guez","year":"2024","journal-title":"Angew. Chem., Int. Ed."},{"issue":"18","key":"2026101414070450800_cit47","doi-asserted-by":"publisher","first-page":"3380","DOI":"10.1002\/ange.200605179","article-title":"Stereospecific Alkyne\nReduction: Novel Activity of Old Yellow Enzymes","volume":"119","author":"Mu\u0308ller","year":"2007","journal-title":"Angew. Chem."},{"issue":"9","key":"2026101414070450800_cit48","doi-asserted-by":"publisher","first-page":"2191","DOI":"10.1002\/cctc.202002011","article-title":"Expanding\nthe Biocatalytic Toolbox\nwith a New Type of ene\/yne-Reductase from Cyclocybe aegerita","volume":"13","author":"Karrer","year":"2021","journal-title":"ChemCatChem."},{"issue":"16","key":"2026101414070450800_cit49","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.202402037","article-title":"Shifting the\nSubstrate Scope of an Ene\/Yne-Reductase by Loop Engineering","volume":"17","author":"Karrer","year":"2025","journal-title":"ChemCatChem."},{"issue":"4","key":"2026101414070450800_cit50","doi-asserted-by":"publisher","first-page":"312","DOI":"10.1038\/s41557-020-00633-7","article-title":"Abiotic\nreduction of ketones with silanes catalysed by carbonic anhydrase\nthrough an enzymatic zinc hydride","volume":"13","author":"Ji","year":"2021","journal-title":"Nat. Chem."},{"issue":"8","key":"2026101414070450800_cit51","doi-asserted-by":"publisher","first-page":"2577","DOI":"10.1016\/j.chempr.2024.06.010","article-title":"Repurposing myoglobin into an abiological\nasymmetric ketoreductase","volume":"10","author":"Zhang","year":"2024","journal-title":"Chem."},{"issue":"36","key":"2026101414070450800_cit52","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202511298","article-title":"Metalloenzyme-Catalyzed Asymmetric\nTransfer Hydrogenation for the Synthesis of Chiral Amines","volume":"64","author":"Cui","year":"2025","journal-title":"Angew. Chem., Int. 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