{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T13:48:59Z","timestamp":1792158539777,"version":"4.4.0"},"reference-count":52,"publisher":"American Chemical Society (ACS)","issue":"41","license":[{"start":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T00:00:00Z","timestamp":1791331200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T00:00:00Z","timestamp":1791331200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T00:00:00Z","timestamp":1791331200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100013066","name":"Key Scientific Research Project of Colleges and Universities in Henan Province","doi-asserted-by":"publisher","award":["26A150011"],"award-info":[{"award-number":["26A150011"]}],"id":[{"id":"10.13039\/501100013066","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001475","name":"Nanyang Technological University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001475","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003489","name":"Henan University of Technology","doi-asserted-by":"publisher","award":["2022BS051"],"award-info":[{"award-number":["2022BS051"]}],"id":[{"id":"10.13039\/501100003489","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003489","name":"Henan University of Technology","doi-asserted-by":"publisher","award":["2024PYJH065"],"award-info":[{"award-number":["2024PYJH065"]}],"id":[{"id":"10.13039\/501100003489","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>We report an aqueous conjugate addition of primary and secondary amines to \u03b2-CF3 alkynones under mild conditions without added metal catalysts or activating reagents. This protocol affords stable, CF3-containing enaminone conjugates in phosphate buffer and is applicable to structurally diverse amine substrates. Its utility is demonstrated by the modification of drugs, amino acid esters, dipeptides, complex bioactive peptides, and proteins, as well as two-step fluorescent labeling of lysozyme confirmed by fluorescence SDS\u2013PAGE analysis.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03805","type":"journal-article","created":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T12:01:35Z","timestamp":1791374495000},"page":"12971-12976","source":"Crossref","is-referenced-by-count":0,"title":["\u03b2-CF3 Alkynones for Amine\nConjugation under Aqueous Conditions"],"prefix":"10.1021","volume":"28","author":[{"given":"Fanyi","family":"Hou","sequence":"first","affiliation":[{"name":"Henan University of Technology , , ,","place":["Zhengzhou, China, 450001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinzan","family":"Feng","sequence":"additional","affiliation":[{"name":"Henan University of Technology , , ,","place":["Zhengzhou, China, 450001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2936-337X","authenticated-orcid":true,"given":"Teck-Peng","family":"Loh","sequence":"additional","affiliation":[{"name":"Henan University of Technology , , ,","place":["Zhengzhou, China, 450001"]},{"name":"Nanyang Technological University , , ,","place":["Singapore, Singapore, 637371"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0006-7655-1468","authenticated-orcid":true,"given":"Yue","family":"Wang","sequence":"additional","affiliation":[{"name":"Henan University of Technology , , ,","place":["Zhengzhou, China, 450001"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,7]]},"reference":[{"key":"2026101608470203000_cit1a","doi-asserted-by":"publisher","first-page":"2169","DOI":"10.1021\/cr078380v","article-title":"Innovations and\nGreen Chemistry","volume":"107","author":"Horva\u0301th","year":"2007","journal-title":"Chem. Rev."},{"key":"2026101608470203000_cit1b","doi-asserted-by":"publisher","first-page":"4417","DOI":"10.1039\/D3GC04183B","article-title":"Controlling\nthe Diffusion of Small Molecules from Matrices Processed by All-Aqueous\nMethodologies: Towards the Development of Green Pharmaceutical Products","volume":"26","author":"Neves","year":"2024","journal-title":"Green Chem."},{"key":"2026101608470203000_cit1c","doi-asserted-by":"publisher","first-page":"232","DOI":"10.1039\/D0GC03447A","article-title":"Recent Advances\nin Visible-Light-Mediated Organic Transformations in Water","volume":"23","author":"Sun","year":"2021","journal-title":"Green Chem."},{"key":"2026101608470203000_cit2a","doi-asserted-by":"publisher","first-page":"7835","DOI":"10.1039\/C9SC03368H","article-title":"Biomedical Applications of Copper-Free\nClick Chemistry: In Vitro, In Vivo, and Ex Vivo","volume":"10","author":"Kim","year":"2019","journal-title":"Chem. Sci."},{"key":"2026101608470203000_cit2b","doi-asserted-by":"publisher","first-page":"13613","DOI":"10.1039\/D1SC02973H","article-title":"Recent\nDevelopments in Chemical Conjugation Strategies Targeting Native Amino\nAcids in Proteins and Their Applications in Antibody\u2013Drug Conjugates","volume":"12","author":"Kang","year":"2021","journal-title":"Chem. Sci."},{"key":"2026101608470203000_cit2c","doi-asserted-by":"publisher","first-page":"774","DOI":"10.1021\/ar2001292","article-title":"Using Synthetically Modified Proteins to Make New Materials","volume":"44","author":"Witus","year":"2011","journal-title":"Acc. Chem. Res."},{"key":"2026101608470203000_cit3a","doi-asserted-by":"publisher","first-page":"2174","DOI":"10.1021\/cr500399p","article-title":"Advances in Chemical Protein Modification","volume":"115","author":"Boutureira","year":"2015","journal-title":"Chem. Rev."},{"key":"2026101608470203000_cit3b","doi-asserted-by":"publisher","first-page":"9829","DOI":"10.1039\/D5SC09331G","article-title":"Recent Advances\nin Site-Specific Modifications of Peptides and Proteins","volume":"17","author":"Duan","year":"2026","journal-title":"Chem. Sci."},{"key":"2026101608470203000_cit3c","doi-asserted-by":"publisher","first-page":"147","DOI":"10.1038\/s41570-019-0079-1","article-title":"Contemporary\nApproaches to Site-Selective Protein Modification","volume":"3","author":"Hoyt","year":"2019","journal-title":"Nat. Rev. Chem."},{"key":"2026101608470203000_cit4a","doi-asserted-by":"publisher","first-page":"2004","DOI":"10.1002\/1521-3773(20010601)40:11&lt;2004::AID-ANIE2004&gt;3.0.CO;2-5","article-title":"Click Chemistry:\nDiverse Chemical Function from a Few Good Reactions","volume":"40","author":"Kolb","year":"2001","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101608470203000_cit4b","doi-asserted-by":"publisher","first-page":"1336","DOI":"10.1039\/D1CS00451D","article-title":"Metal-Free Bioorthogonal Click Chemistry\nin Cancer Theranostics","volume":"51","author":"Wu","year":"2022","journal-title":"Chem. Soc. Rev."},{"key":"2026101608470203000_cit4c","doi-asserted-by":"publisher","first-page":"7122","DOI":"10.1021\/acs.chemrev.0c00928","article-title":"A Hitchhiker\u2019s\nGuide to Click-Chemistry with Nucleic Acids","volume":"121","author":"Fantoni","year":"2021","journal-title":"Chem. Rev."},{"key":"2026101608470203000_cit5a","doi-asserted-by":"publisher","first-page":"70","DOI":"10.1021\/acs.accounts.3c00555","article-title":"Development and Applications of Water-Compatible\nReactions: A Journey to Be Continued","volume":"57","author":"Lu","year":"2024","journal-title":"Acc. Chem.\nRes."},{"key":"2026101608470203000_cit5b","doi-asserted-by":"publisher","first-page":"8451","DOI":"10.1021\/acs.langmuir.4c05355","article-title":"Green Catalysis: Water as a Sustainable Medium in Organocatalyzed\nReactions","volume":"41","author":"Fatima","year":"2025","journal-title":"Langmuir"},{"key":"2026101608470203000_cit6a","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.202400715","article-title":"Covalent\nModification of Protein by Chemical Probe in Living Cells for Structural\nand Interaction Studies","volume":"26","author":"Zheng","year":"2025","journal-title":"ChemBioChem"},{"key":"2026101608470203000_cit6b","doi-asserted-by":"publisher","first-page":"23084","DOI":"10.1002\/anie.202101502","article-title":"To View Your Biomolecule,\nClick inside the Cell","volume":"60","author":"Rigolot","year":"2021","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101608470203000_cit7a","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202501565","article-title":"Protein N-Terminal\nModification: Recent Advances in Chemical and Enzymatic Strategies","volume":"31","author":"Fan","year":"2025","journal-title":"Chem.\u2500Eur. J."},{"key":"2026101608470203000_cit7b","doi-asserted-by":"publisher","first-page":"240","DOI":"10.1016\/j.trechm.2025.03.003","article-title":"Site-Selective\nModification of Native Proteins","volume":"7","author":"Kim","year":"2025","journal-title":"Trends Chem."},{"key":"2026101608470203000_cit7c","doi-asserted-by":"publisher","first-page":"e71193","DOI":"10.1002\/chem.71193","article-title":"Precision Chemistry for Protein Lysine\nModification","volume":"32","author":"Onoda","year":"2026","journal-title":"Chem.\u2500Eur. J."},{"key":"2026101608470203000_cit8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202111783","article-title":"Azaphilones as Activation-Free\nPrimary-Amine-Specific Bioconjugation Reagents for Peptides, Proteins\nand Lipids","volume":"61","author":"Yi","year":"2022","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101608470203000_cit9a","doi-asserted-by":"publisher","first-page":"1181","DOI":"10.1038\/nchem.2826","article-title":"Global Profiling\nof Lysine Reactivity\nand Ligandability in the Human Proteome","volume":"9","author":"Hacker","year":"2017","journal-title":"Nat.\nChem."},{"key":"2026101608470203000_cit9b","doi-asserted-by":"publisher","first-page":"631","DOI":"10.1038\/s41594-018-0084-y","article-title":"UbiSite Approach\nfor Comprehensive Mapping of Lysine and N-Terminal Ubiquitination\nSites","volume":"25","author":"Akimov","year":"2018","journal-title":"Nat. Struct. Mol. Biol."},{"key":"2026101608470203000_cit10","doi-asserted-by":"publisher","first-page":"697","DOI":"10.1038\/nchembio.2416","article-title":"Targeting the N\nTerminus for Site-Selective Protein\nModification","volume":"13","author":"Rosen","year":"2017","journal-title":"Nat. Chem. Biol."},{"key":"2026101608470203000_cit11a","doi-asserted-by":"publisher","first-page":"2416","DOI":"10.1021\/ja026917a","article-title":"A Modular\nCross-Linking\nApproach for Exploring Protein Interactions","volume":"125","author":"Trester-Zedlitz","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"2026101608470203000_cit11b","doi-asserted-by":"publisher","first-page":"500","DOI":"10.1021\/bc200556n","article-title":"Site-Selective\nLysine Modification of Native Proteins and Peptides via Kinetically\nControlled Labeling","volume":"23","author":"Chen","year":"2012","journal-title":"Bioconjugate Chem."},{"key":"2026101608470203000_cit12a","doi-asserted-by":"publisher","first-page":"1321","DOI":"10.1002\/cbic.200900132","article-title":"[18F]SiFA-Isothiocyanate: A New Highly Effective\nRadioactive Labeling Agent for Lysine-Containing Proteins","volume":"10","author":"Rosa-Neto","year":"2009","journal-title":"ChemBioChem."},{"key":"2026101608470203000_cit12b","doi-asserted-by":"publisher","first-page":"409","DOI":"10.1021\/bc200401b","article-title":"Reagents\nfor Astatination of Biomolecules. 6. An Intact Antibody Conjugated\nwith a Maleimido-closo-Decaborate(2\u2212) Reagent\nvia Sulfhydryl Groups Had Considerably Higher Kidney Concentrations\nthan the Same Antibody Conjugated with an Isothiocyanato-closo-Decaborate(2\u2212) Reagent via Lysine Amines","volume":"23","author":"Wilbur","year":"2012","journal-title":"Bioconjugate Chem."},{"key":"2026101608470203000_cit13","doi-asserted-by":"publisher","first-page":"4004","DOI":"10.1021\/jacs.7b12874","article-title":"Chemo-\nand Regioselective Lysine Modification on Native Proteins","volume":"140","author":"Matos","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"2026101608470203000_cit14a","doi-asserted-by":"publisher","first-page":"2198","DOI":"10.1021\/acs.accounts.8b00154","article-title":"Versatile Bioconjugation\nChemistries of ortho-Boronyl Aryl Ketones and Aldehydes","volume":"51","author":"Cambray","year":"2018","journal-title":"Acc. Chem. Res."},{"key":"2026101608470203000_cit14b","doi-asserted-by":"publisher","first-page":"1585","DOI":"10.1039\/D0SC05009A","article-title":"Boronic Acid\nBased Dynamic Click Chemistry: Recent Advances and Emergent Applications","volume":"12","author":"Chatterjee","year":"2021","journal-title":"Chem. Sci."},{"key":"2026101608470203000_cit15a","doi-asserted-by":"publisher","first-page":"2600","DOI":"10.1021\/acs.orglett.6b00983","article-title":"Traceless\nand Chemoselective Amine Bioconjugation via\nPhthalimidine Formation in Native Protein Modification","volume":"18","author":"Tung","year":"2016","journal-title":"Org. Lett."},{"key":"2026101608470203000_cit15b","doi-asserted-by":"publisher","first-page":"1422","DOI":"10.1021\/acs.bioconjchem.7b00106","article-title":"General Dialdehyde Click Chemistry for Amine Bioconjugation","volume":"28","author":"Elahipanah","year":"2017","journal-title":"Bioconjugate Chem."},{"key":"2026101608470203000_cit16","doi-asserted-by":"publisher","first-page":"5495","DOI":"10.1039\/C5CS00048C","article-title":"Developments and Recent\nAdvancements in the Field of\nEndogenous Amino Acid Selective Bond Forming Reactions for Bioconjugation","volume":"44","author":"Koniev","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"2026101608470203000_cit17a","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.adg4924","article-title":"Alkynone \u03b2-Trifluoroborates:\nA New Class of Amine-Specific\nBiocompatible Click Reagents","volume":"9","author":"Teng","year":"2023","journal-title":"Sci. Adv."},{"key":"2026101608470203000_cit17b","doi-asserted-by":"publisher","DOI":"10.1016\/j.xinn.2025.101013","article-title":"\u03b2-Alkoxy\nEnones for Biocompatible Primary Amine Conjugation","volume":"6","author":"Zhang","year":"2025","journal-title":"Innovation"},{"key":"2026101608470203000_cit17c","doi-asserted-by":"publisher","first-page":"1553","DOI":"10.1021\/acs.bioconjchem.3c00246","volume":"34","author":"Gao","year":"2023","journal-title":"Bioconjugate Chem."},{"key":"2026101608470203000_cit18a","doi-asserted-by":"publisher","first-page":"9187","DOI":"10.1021\/acs.chemrev.5c00154","article-title":"Chemistry\nof Bis(trifluoromethyl)amines:\nSynthesis, Properties, and Applications","volume":"125","author":"Ignat\u2019ev","year":"2025","journal-title":"Chem.\nRev."},{"key":"2026101608470203000_cit18b","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2021.109762","article-title":"Oxidative Trifluoromethyl(thiol\/selenol)ation\nof Terminal Alkynes: An Overview","volume":"245","author":"Hassanpour","year":"2021","journal-title":"J. Fluorine\nChem."},{"key":"2026101608470203000_cit19","doi-asserted-by":"publisher","first-page":"108","DOI":"10.1111\/cas.13106","article-title":"Celecoxib and 2,5-Dimethylcelecoxib\nInhibit Intestinal Cancer Growth by Suppressing the Wnt\/\u03b2-Catenin\nSignaling Pathway","volume":"108","author":"Egashira","year":"2017","journal-title":"Cancer Sci."},{"key":"2026101608470203000_cit20","doi-asserted-by":"publisher","first-page":"686","DOI":"10.1093\/jpp\/rgad016","article-title":"Gap Junction\nIs Essential for the Antidepressant Effects of Fluoxetine","volume":"75","author":"Xia","year":"2023","journal-title":"J. Pharm. Pharmacol."},{"key":"2026101608470203000_cit21","doi-asserted-by":"publisher","first-page":"699","DOI":"10.1093\/jac\/dky481","article-title":"Pharmacogenetics and\nPharmacokinetics of CNS Penetration of Efavirenz and Its Metabolites","volume":"74","author":"Decloedt","year":"2019","journal-title":"J. Antimicrob. Chemother."},{"key":"2026101608470203000_cit22","doi-asserted-by":"publisher","first-page":"331","DOI":"10.3350\/cmh.2018.0006","article-title":"Combined Effects of Synbiotic and\nSitagliptin versus Sitagliptin Alone in Patients with Nonalcoholic\nFatty Liver Disease","volume":"24","author":"Sayari","year":"2018","journal-title":"Clin. Mol. Hepatol."},{"key":"2026101608470203000_cit23a","doi-asserted-by":"publisher","first-page":"1662","DOI":"10.1039\/C8GC00078F","article-title":"Fluoroalkylation Reactions in Aqueous Media: A Review","volume":"20","author":"Song","year":"2018","journal-title":"Green Chem."},{"key":"2026101608470203000_cit23b","doi-asserted-by":"publisher","first-page":"3951","DOI":"10.1039\/C7GC01566F","article-title":"Recent\nProgress on Fluorination in Aqueous Media","volume":"19","author":"Yang","year":"2017","journal-title":"Green\nChem."},{"key":"2026101608470203000_cit23c","doi-asserted-by":"publisher","first-page":"898","DOI":"10.1002\/ajoc.202000170","article-title":"Site-Selective Trifluoromethylation\nReactions of Oligopeptides","volume":"9","author":"Guerrero","year":"2020","journal-title":"Asian J. Org. Chem."},{"key":"2026101608470203000_cit24a","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202408220","article-title":"Rhodium-Catalyzed Asymmetric Cyclopropanation of Indoles with N-Triftosylhydrazones","volume":"63","author":"He","year":"2024","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026101608470203000_cit24b","doi-asserted-by":"publisher","first-page":"10010","DOI":"10.1039\/D5GC01349F","article-title":"Visible-Light-Induced and EDA Complex-Driven\nMulticomponent Reaction: A Strategy for the Synthesis of \u03b1-CF3-\u03b2-Phosphorodithioate Tertiary Alcohols","volume":"27","author":"Wang","year":"2025","journal-title":"Green Chem."},{"key":"2026101608470203000_cit25a","doi-asserted-by":"publisher","first-page":"2753","DOI":"10.1039\/D5GC06237C","article-title":"Photocatalytic Carbamoylation to\nAccess Thiocarbonyl Amino Acid\/Peptide Derivatives in a Sustainable\nSolvent","volume":"28","author":"Zeng","year":"2026","journal-title":"Green Chem."},{"key":"2026101608470203000_cit25b","doi-asserted-by":"publisher","first-page":"781","DOI":"10.31635\/ccschem.025.202506216","article-title":"Alkynyl\nAldehyde: A Thiol-Specific Reagent Carrying a Versatile Formyl Group","volume":"8","author":"Li","year":"2026","journal-title":"CCS Chem."},{"key":"2026101608470203000_cit25c","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.adp7544","article-title":"\u03b2-Silyl Alkynoates:\nVersatile Reagents for Biocompatible and Selective Amide Bond Formation","volume":"10","author":"Choudhuri","year":"2024","journal-title":"Sci. Adv."},{"key":"2026101608470203000_cit25d","doi-asserted-by":"publisher","first-page":"1776","DOI":"10.1021\/jacs.3c12050","article-title":"Silicon-Containing Thiol-Specific\nBioconjugating Reagent","volume":"146","author":"Zhang","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026101608470203000_cit25e","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202311906","article-title":"Thiol-Specific Silicon-Containing\nConjugating Reagent: \u03b2-Silyl Alkynyl Carbonyl Compounds","volume":"62","author":"Teng","year":"2023","journal-title":"Angew. Chem., Int. Ed."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.6c03805","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/doi\/10.1021\/acs.orglett.6c03805\/68768084\/acs.orglett.6c03805.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/doi\/10.1021\/acs.orglett.6c03805\/68768084\/acs.orglett.6c03805.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T13:03:53Z","timestamp":1792155833000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/orlef7\/article\/28\/41\/12971\/5445908\/CF3-Alkynones-for-Amine-Conjugation-under-Aqueous"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,10,7]]},"references-count":52,"journal-issue":{"issue":"41","published-online":{"date-parts":[[2026,10,7]]},"published-print":{"date-parts":[[2026,10,16]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.6c03805","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,10,7]]}}}