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While enzymes excel in achieving unparalleled selectivity, their inherent specificity often confines activity to a single stereoisomeric substrate, consequently restricting the overall efficiency of such transformations. Here, we demonstrate that protoglobin-derived hemoproteins can catalyze stereoconvergent intermolecular amination using simple N-alkyl hydroxylamines as nitrene precursors, a transformation which remains elusive in synthetic chemistry. These engineered enzymes process E\/Z mixtures of silyl enol ethers, enabling the precise incorporation of N-alkyl amino moieties (\u2212NHAlkyl) into diverse molecular structures (up to 79% yield and 95% ee). Two complementary protoglobin variants were engineered using directed evolution to enable enantiodivergent synthesis of both enantiomers of \u03b1-aminoketones. This enzymatic platform achieves stereoconvergent and enantiodivergent transformations, facilitating the conversion of simple chemicals into an array of valuable pharmaceutical compounds featuring aminoketone functionalities.<\/jats:p>","DOI":"10.1021\/jacs.5c17989","type":"journal-article","created":{"date-parts":[[2026,5,1]],"date-time":"2026-05-01T11:54:32Z","timestamp":1777636472000},"page":"18555-18561","source":"Crossref","is-referenced-by-count":1,"title":["Engineering Enantiocomplementary\nProtoglobins for\nStereoconvergent Construction of\n                    <i>N<\/i>\n                    -Alkylated\n\u03b1-Aminoketones"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7356-6927","authenticated-orcid":true,"given":"Zi-Yang","family":"Qin","sequence":"first","affiliation":[{"name":"California Institute of Technology , , , ,","place":["Pasadena, California, United States, 91125"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1353-3004","authenticated-orcid":true,"given":"Zi-Qi","family":"Li","sequence":"additional","affiliation":[{"name":"California Institute of Technology , , , ,","place":["Pasadena, California, United States, 91125"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-4316-3576","authenticated-orcid":true,"given":"Chi","family":"Zhang","sequence":"additional","affiliation":[{"name":"California Institute of Technology , , , ,","place":["Pasadena, California, United States, 91125"]},{"name":"California Institute of Technology , , , ,","place":["Pasadena, California, United States, 91125"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jan L.","family":"Heise","sequence":"additional","affiliation":[{"name":"California Institute of Technology , , , ,","place":["Pasadena, California, United States, 91125"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4678-7251","authenticated-orcid":true,"given":"Runze","family":"Mao","sequence":"additional","affiliation":[{"name":"California Institute of Technology , , , ,","place":["Pasadena, California, United States, 91125"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sophia J.","family":"Wu","sequence":"additional","affiliation":[{"name":"California Institute of Technology , , , ,","place":["Pasadena, California, United States, 91125"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8387-5261","authenticated-orcid":true,"given":"K. N.","family":"Houk","sequence":"additional","affiliation":[{"name":"University of California , , Los Angeles , , ,","place":["Los Angeles, California, United States, 90095"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0097-5716","authenticated-orcid":true,"given":"William A.","family":"Goddard III","sequence":"additional","affiliation":[{"name":"California Institute of Technology , , , ,","place":["Pasadena, California, United States, 91125"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Frances H.","family":"Arnold","sequence":"additional","affiliation":[{"name":"California Institute of Technology , , , ,","place":["Pasadena, California, United States, 91125"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,5,1]]},"reference":[{"key":"2026090713182576000_cit1","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\nReactions","volume":"55","author":"Wu","year":"2019","journal-title":"Chem. 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Res."},{"key":"2026090713182576000_cit5","doi-asserted-by":"publisher","first-page":"2650","DOI":"10.1021\/acs.chemrev.1c00324","article-title":"Advances in the E \u2192 Z Isomerization\nof Alkenes Using Small Molecule\nPhotocatalysts","volume":"122","author":"Nevesely\u0301","year":"2022","journal-title":"Chem. Rev."},{"key":"2026090713182576000_cit6","doi-asserted-by":"publisher","first-page":"1348","DOI":"10.1002\/adsc.202200199","article-title":"E\/Z Photoisomerization of Olefins\nas an Emergent Strategy for the Control of Stereodivergence in Catalysis","volume":"364","author":"Corpas","year":"2022","journal-title":"Adv. Synth. Catal."},{"key":"2026090713182576000_cit7","doi-asserted-by":"publisher","first-page":"146","DOI":"10.1021\/ar00051a008","article-title":"Biomimetic\nChemistry and Artificial Enzymes: Catalysis by Design","volume":"28","author":"Breslow","year":"1995","journal-title":"Acc. Chem. 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Lett."},{"key":"2026090713182576000_cit29","doi-asserted-by":"publisher","first-page":"467","DOI":"10.1016\/j.tibs.2025.01.009","article-title":"From Lead\nto Market: Chemical Approaches\nto Transform Peptides into Therapeutics","volume":"50","author":"Gare","year":"2025","journal-title":"Trends\nBiochem. Sci."},{"key":"2026090713182576000_cit30","doi-asserted-by":"publisher","first-page":"36968","DOI":"10.1074\/jbc.M111.265249","article-title":"Non-Equivalent Role of Inter- and\nIntramolecular Hydrogen Bonds in the Insulin Dimer Interface","volume":"286","author":"Antoli\u0301kova\u0301","year":"2011","journal-title":"J. Biol. 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Med.\nChem."},{"key":"2026090713182576000_cit34","doi-asserted-by":"publisher","first-page":"2228","DOI":"10.1021\/jm970161m","article-title":"Design of a Potent\nCombined Pseudopeptide Endothelin-A\/Endothelin-B Receptor Antagonist,\nAc-dBhg16-Leu-Asp-Ile-[NMe]Ile-Trp21 (PD 156252):\nExamination of Its Pharmacokinetic and Spectral Properties","volume":"40","author":"Cody","year":"1997","journal-title":"J. Med. Chem."},{"key":"2026090713182576000_cit35","doi-asserted-by":"publisher","first-page":"1344","DOI":"10.1038\/s41467-017-01428-0","article-title":"Convenient Iron-Catalyzed\nReductive Aminations without Hydrogen for Selective Synthesis of N-Methylamines","volume":"8","author":"Natte","year":"2017","journal-title":"Nat. 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