{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T09:12:03Z","timestamp":1788513123942,"version":"build-2803163510"},"reference-count":33,"publisher":"American Chemical Society (ACS)","issue":"6","license":[{"start":{"date-parts":[[2018,6,6]],"date-time":"2018-06-06T00:00:00Z","timestamp":1528243200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/501100001407","name":"Department of Biotechnology , Ministry of Science and Technology","doi-asserted-by":"publisher","award":["BT\/PR16164\/NER\/95\/88\/2015"],"award-info":[{"award-number":["BT\/PR16164\/NER\/95\/88\/2015"]}],"id":[{"id":"10.13039\/501100001407","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2018,6,30]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Here, the synthesis and applications of (E)-ethyl-2-cyano-2-(((2,4,6-trichlorobenzoyl)oxy)imino)acetate as a racemization suppressing and easily recyclable version of the Yamaguchi reagent that can be used for amide and peptide synthesis are reported. We demonstrated its application in racemization-free esterification, thioesterification, amidation, and peptide bond formation. We successfully synthesized oligopeptides on the solid support in dimethylformamide as well as in solution (dichloromethane) by applying this coupling reagent. It is important to note that a mixed-anhydride-based method provides peptide-forming reactions as good as the current methods using built-in coupling reagents. Mechanism investigation, racemization suppression, and recyclability are also discussed.<\/jats:p>","DOI":"10.1021\/acsomega.8b00732","type":"journal-article","created":{"date-parts":[[2018,6,6]],"date-time":"2018-06-06T12:42:19Z","timestamp":1528288939000},"page":"6120-6133","source":"Crossref","is-referenced-by-count":16,"title":["(\n                    <i>E<\/i>\n                    )-Ethyl-2-cyano-2-(((2,4,6-trichlorobenzoyl)oxy)imino)acetate: A Modified Yamaguchi Reagent for\nEnantioselective Esterification, Thioesterification, Amidation, and\nPeptide Synthesis"],"prefix":"10.1021","volume":"3","author":[{"given":"Jyoti","family":"Chandra","sequence":"first","affiliation":[{"name":"Indian Institute of Technology Guwahati , , , ,","place":["Guwahati, Assam, India, 781039"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Srinivasa Rao","family":"Manne","sequence":"additional","affiliation":[{"name":"Indian Institute of Technology Guwahati , , , ,","place":["Guwahati, Assam, India, 781039"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sandip","family":"Mondal","sequence":"additional","affiliation":[{"name":"Indian Institute of Technology Guwahati , , , ,","place":["Guwahati, Assam, India, 781039"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3435-5443","authenticated-orcid":true,"given":"Bhubaneswar","family":"Mandal","sequence":"additional","affiliation":[{"name":"Indian Institute of Technology Guwahati , , , ,","place":["Guwahati, Assam, India, 781039"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2018,6,6]]},"reference":[{"key":"2026090320091895400_cit1","doi-asserted-by":"publisher","first-page":"2243","DOI":"10.1021\/cr950005s","article-title":"Chemical Synthesis of Natural Product Peptides: Coupling\nMethods for the Incorporation of Non-coded Amino Acids into Peptides","volume":"97","author":"Humphrey","year":"1997","journal-title":"Chem. Rev."},{"key":"2026090320091895400_cit2","doi-asserted-by":"publisher","first-page":"55","DOI":"10.1021\/cc9800071","article-title":"A Knowledge-Based Approach in Designing\nCombinatorial or Medicinal Chemistry Libraries for Drug Discovery.\n1. A Qualitative and Quantitative Characterization of Known Drug Databases","volume":"1","author":"Ghose","year":"1999","journal-title":"J. Comb. Chem."},{"key":"2026090320091895400_cit3","doi-asserted-by":"publisher","first-page":"6557","DOI":"10.1021\/cr100048w","article-title":"Peptide Coupling\nReagents, More than a Letter Soup","volume":"111","author":"El-Faham","year":"2011","journal-title":"Chem. Rev."},{"key":"2026090320091895400_cit4","first-page":"980","volume-title":"Comprehensive Organic\nTransformations","author":"Larock","year":"1989"},{"key":"2026090320091895400_cit5","doi-asserted-by":"publisher","first-page":"4408","DOI":"10.1021\/ja028694u","article-title":"Stereoselective Synthesis\nof \u03b1- and \u03b2-Glycosylamide\nDerivatives from Glycopyranosyl Azides via Isoxazoline Intermediates","volume":"125","author":"Damkaci","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"2026090320091895400_cit6","doi-asserted-by":"publisher","first-page":"5002","DOI":"10.1021\/ja101292a","article-title":"Nucleophilic Acyl Substitution via Aromatic Cation\nActivation of Carboxylic Acids: Rapid Generation of Acid Chlorides\nunder Mild Conditions","volume":"132","author":"Hardee","year":"2010","journal-title":"J. Am. Chem. 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Org.\nChem."},{"key":"2026090320091895400_cit10","doi-asserted-by":"publisher","first-page":"1989","DOI":"10.1246\/bcsj.52.1989","article-title":"A Rapid Esterification\nby Means of Mixed Anhydride and Its Application to Large-ring Lactonization","volume":"52","author":"Inanaga","year":"1979","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"2026090320091895400_cit11a","doi-asserted-by":"publisher","first-page":"7535","DOI":"10.1016\/S0040-4039(02)01819-1","article-title":"A novel and\nefficient macrolactonization of \u03c9-hydroxycarboxylic acids using\n2-methyl-6-nitrobenzoic anhydride (MNBA)","volume":"43","author":"Shiina","year":"2002","journal-title":"Tetrahedron\nLett."},{"key":"2026090320091895400_cit11b","doi-asserted-by":"publisher","first-page":"4413","DOI":"10.1021\/ja00120a030","article-title":"Scandium Trifluoromethanesulfonate\nas an Extremely Active Acylation Catalyst","volume":"117","author":"Ishihara","year":"1995","journal-title":"J.\nAm. Chem. 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Sci."},{"key":"2026090320091895400_cit16b","first-page":"21","article-title":"Low-epimerization Peptide Bond Formation with Oxyma\nPure: Preparation of Z-L-Phg-Val-OMe","volume":"46","author":"Subiro\u0301s-Funosas","year":"2013","journal-title":"Aldrichim.\nActa"},{"key":"2026090320091895400_cit17a","doi-asserted-by":"publisher","first-page":"5420","DOI":"10.1021\/jo500292m","article-title":"Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate\n(o-NosylOXY): A Recyclable Coupling Reagent for Racemization-Free\nSynthesis of Peptide, Amide, Hydroxamate, and Ester","volume":"79","author":"Dev","year":"2014","journal-title":"J. Org. 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Chem."},{"key":"2026090320091895400_cit17d","doi-asserted-by":"publisher","first-page":"4397","DOI":"10.1016\/j.tetlet.2013.05.149","article-title":"An unexpected\ninvolvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product\nin the promotion of the synthesis of nitriles from aldoximes: a mechanistic\nperception","volume":"54","author":"Dev","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"2026090320091895400_cit17e","doi-asserted-by":"publisher","first-page":"168","DOI":"10.1002\/adsc.201600661","article-title":"Ethyl 2-(tert-Butoxycarbonyloxyimino)-2-cyanoacetate\n(Boc-Oxyma): An Efficient Reagent for the Racemization Free Synthesis\nof Ureas, Carbamates and Thiocarbamates via Lossen Rearrangement","volume":"359","author":"Manne","year":"2017","journal-title":"Adv. Synth. 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Catal."},{"key":"2026090320091895400_cit18","doi-asserted-by":"publisher","first-page":"522","DOI":"10.1002\/anie.197805221","article-title":"Simple Method for the\nEsterification of Carboxylic\nAcids","volume":"17","author":"Neises","year":"1978","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090320091895400_cit19","doi-asserted-by":"publisher","first-page":"2731","DOI":"10.1021\/jo702622c","article-title":"Morpholine-Based Immonium and Halogenoamidinium Salts\nas Coupling Reagents in Peptide Synthesis","volume":"73","author":"El-Faham","year":"2008","journal-title":"J.\nOrg. Chem."},{"key":"2026090320091895400_cit20","doi-asserted-by":"publisher","first-page":"5642","DOI":"10.1046\/j.1432-1033.2002.03271.x","article-title":"Solution structure\nof the Alzheimer amyloid \u03b2-peptide (1-42) in an apolar microenvironment","volume":"269","author":"Crescenzi","year":"2002","journal-title":"Eur. J. Biochem."},{"key":"2026090320091895400_cit21","doi-asserted-by":"publisher","first-page":"8328","DOI":"10.1002\/anie.200903888","article-title":"Tunable, Temperature-Responsive Polynorbornenes with\nSide Chains Based on an Elastin Peptide Sequence","volume":"48","author":"Conrad","year":"2009","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090320091895400_cit22","doi-asserted-by":"publisher","first-page":"3020","DOI":"10.1021\/ol301085v","article-title":"Recyclable Hypervalent\nIodine(III) Reagent Iodosodilactone as an Efficient Coupling Reagent\nfor Direct Esterification, Amidation, and Peptide Coupling","volume":"14","author":"Tian","year":"2012","journal-title":"Org. Lett."},{"key":"2026090320091895400_cit23","doi-asserted-by":"publisher","first-page":"279","DOI":"10.1016\/S0040-4039(00)83996-9","article-title":"The use of microwave\novens for rapid\norganic synthesis","volume":"27","author":"Gedye","year":"1986","journal-title":"Tetrahedron Lett."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.8b00732","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/3\/6\/6120\/68320166\/acsomega.8b00732.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/3\/6\/6120\/68320166\/acsomega.8b00732.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T08:14:38Z","timestamp":1788509678000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/3\/6\/6120\/744905\/E-Ethyl-2-cyano-2-2-4-6-trichlorobenzoyl-oxy-imino"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,6,6]]},"references-count":33,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2018,6,6]]},"published-print":{"date-parts":[[2018,6,30]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.8b00732","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,6,6]]}}}