{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,17]],"date-time":"2026-06-17T04:50:28Z","timestamp":1781671828143,"version":"3.54.5"},"reference-count":95,"publisher":"Wiley","issue":"34","license":[{"start":{"date-parts":[[2025,4,16]],"date-time":"2025-04-16T00:00:00Z","timestamp":1744761600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100019108","name":"National Chemical Laboratory","doi-asserted-by":"publisher","award":["TSP024026"],"award-info":[{"award-number":["TSP024026"]}],"id":[{"id":"10.13039\/501100019108","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2025,6,17]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    The merger of peptide and heterocyclic chemistry presents significant opportunities for enhancing the structural and functional diversity of therapeutic agents. In this study, we introduce a streamlined on\u2010resin method to modify peptides at the\n                    <jats:italic>N<\/jats:italic>\n                    \u2010terminus amines and the side chain amines of Lys\/Orn amino acids by incorporating the biologically active triazolobenzodiazepine scaffold. In the presented solid\u2010phase peptide synthesis (SPPS), the triazolobenzodiazepine core is formed on\u2010resin through a combination of\n                    <jats:italic>N<\/jats:italic>\n                    \u2010alkylation, amide bond formation, and an alkyne\u2010azide 1,3\u2010dipolar cycloaddition, of which the latter two happen as a single\u2010step one\u2010pot reaction\u2010 proceeding under mild conditions without metal catalysts. This protocol tolerates a wide variety of amino acids and functional groups, providing a versatile method for synthesizing peptide\u2010triazolobenzodiazepine hybrids. Using orthogonal protection group strategies, we further demonstrate the method's adaptability for two site modifications in peptides involving both the\n                    <jats:italic>N<\/jats:italic>\n                    \u2010terminus and Lys side chain amines. These modifications enhance the scope of \u201cpeptide medicinal chemistry\u201d by creating multifunctional peptides with potential therapeutic applications. The method's compatibility with SPPS, room temperature conditions, and elimination of metal catalysis make it an efficient and powerful tool for peptide modification.\n                  <\/jats:p>","DOI":"10.1002\/chem.202500836","type":"journal-article","created":{"date-parts":[[2025,4,16]],"date-time":"2025-04-16T05:41:06Z","timestamp":1744782066000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Peptide\u2010Triazolobenzodiazepine Hybrids: A Catalyst\u2010Free on\u2010Resin Strategy to Build Complex Therapeutic Motifs Into Peptides"],"prefix":"10.1002","volume":"31","author":[{"given":"Sandip Sushila Mohan","family":"Kamble","sequence":"first","affiliation":[{"name":"Division of Organic Chemistry CSIR\u2010National Chemical Laboratory  Dr. Homi Bhabha Road Pune 411008 India"},{"name":"Central NMR Facility CSIR\u2010National Chemical Laboratory  Dr. Homi Bhabha Road Pune 411008 India"},{"name":"CSIR\u2010HRDC Campus Academy of Scientific and Innovative Research (AcSIR)  Sector 19, Kamla Nehru Nagar Ghaziabad Uttar Pradesh 201002 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Supriya Mahadev","family":"Bodake","sequence":"additional","affiliation":[{"name":"Division of Organic Chemistry CSIR\u2010National Chemical Laboratory  Dr. Homi Bhabha Road Pune 411008 India"},{"name":"Central NMR Facility CSIR\u2010National Chemical Laboratory  Dr. Homi Bhabha Road Pune 411008 India"},{"name":"CSIR\u2010HRDC Campus Academy of Scientific and Innovative Research (AcSIR)  Sector 19, Kamla Nehru Nagar Ghaziabad Uttar Pradesh 201002 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0466-6611","authenticated-orcid":false,"given":"Udaya Kiran","family":"Marelli","sequence":"additional","affiliation":[{"name":"Division of Organic Chemistry CSIR\u2010National Chemical Laboratory  Dr. Homi Bhabha Road Pune 411008 India"},{"name":"Central NMR Facility CSIR\u2010National Chemical Laboratory  Dr. Homi Bhabha Road Pune 411008 India"},{"name":"CSIR\u2010HRDC Campus Academy of Scientific and Innovative Research (AcSIR)  Sector 19, Kamla Nehru Nagar Ghaziabad Uttar Pradesh 201002 India"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,4,16]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules28207165"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.7883\/yoken.JJID.2017.090"},{"key":"e_1_2_8_2_3","doi-asserted-by":"publisher","DOI":"10.1038\/s41573-020-00135-8"},{"key":"e_1_2_8_2_4","doi-asserted-by":"publisher","DOI":"10.1016\/j.drudis.2014.10.003"},{"key":"e_1_2_8_2_5","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00556H"},{"key":"e_1_2_8_2_6","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00522"},{"key":"e_1_2_8_2_7","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB00133F"},{"key":"e_1_2_8_2_8","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA10127C"},{"key":"e_1_2_8_2_9","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c03168"},{"key":"e_1_2_8_2_10","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c02289"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c00269"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2636"},{"key":"e_1_2_8_3_3","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB00907E"},{"key":"e_1_2_8_3_4","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0802300105"},{"key":"e_1_2_8_3_5","doi-asserted-by":"publisher","DOI":"10.3390\/molecules18089797"},{"key":"e_1_2_8_3_6","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26102937"},{"key":"e_1_2_8_3_7","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202304740"},{"key":"e_1_2_8_3_8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201912902"},{"key":"e_1_2_8_3_9","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202407764"},{"key":"e_1_2_8_3_10","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202420522"},{"key":"e_1_2_8_3_11","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c00580"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00789"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700728"},{"key":"e_1_2_8_4_3","doi-asserted-by":"publisher","DOI":"10.3390\/ph5030297"},{"key":"e_1_2_8_4_4","doi-asserted-by":"publisher","DOI":"10.3390\/antibiotics12030532"},{"key":"e_1_2_8_4_5","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-021-20992-0"},{"key":"e_1_2_8_4_6","doi-asserted-by":"publisher","DOI":"10.3390\/md18040203"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2021.06.011"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6SC04744K"},{"key":"e_1_2_8_5_3","doi-asserted-by":"publisher","DOI":"10.1021\/ja208009r"},{"key":"e_1_2_8_5_4","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c04894"},{"key":"e_1_2_8_5_5","doi-asserted-by":"publisher","DOI":"10.1002\/pmic.201400619"},{"key":"e_1_2_8_5_6","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc42261e"},{"key":"e_1_2_8_5_7","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202205368"},{"key":"e_1_2_8_5_8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202104780"},{"key":"e_1_2_8_5_9","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c03389"},{"key":"e_1_2_8_5_10","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c04071"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB01866E"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b03982"},{"key":"e_1_2_8_6_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201405924"},{"key":"e_1_2_8_6_4","doi-asserted-by":"publisher","DOI":"10.1080\/14686996.2017.1411143"},{"key":"e_1_2_8_6_5","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202404747"},{"key":"e_1_2_8_6_6","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201812620"},{"key":"e_1_2_8_6_7","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c04498"},{"key":"e_1_2_8_6_8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202318893"},{"key":"e_1_2_8_6_9","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202405344"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202300753"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1QO00892G"},{"key":"e_1_2_8_7_3","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2023.106892"},{"key":"e_1_2_8_7_4","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60384a"},{"key":"e_1_2_8_7_5","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.7b00001"},{"key":"e_1_2_8_7_6","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c13825"},{"key":"e_1_2_8_7_7","doi-asserted-by":"publisher","DOI":"10.1039\/D3QO01980B"},{"key":"e_1_2_8_7_8","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202401716"},{"key":"e_1_2_8_7_9","doi-asserted-by":"publisher","DOI":"10.1021\/ol0518028"},{"key":"e_1_2_8_7_10","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c03284"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201800458"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b03623"},{"key":"e_1_2_8_8_3","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.4c02654"},{"key":"e_1_2_8_8_4","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.9b00515"},{"key":"e_1_2_8_8_5","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201900692"},{"key":"e_1_2_8_8_6","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202111783"},{"key":"e_1_2_8_8_7","doi-asserted-by":"publisher","DOI":"10.3390\/molecules28031083"},{"key":"e_1_2_8_8_8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202402880"},{"key":"e_1_2_8_8_9","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202301543"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/s42004-020-0309-y"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.202100323"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c00766"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202320012"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/tx00005a002"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2005.12.003"},{"key":"e_1_2_8_13_3","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-5198(19)36199-2"},{"key":"e_1_2_8_13_4","doi-asserted-by":"publisher","DOI":"10.1111\/j.1476-5381.1985.tb08952.x"},{"key":"e_1_2_8_13_5","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.7b00389"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11030-019-09940-9"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00178a010"},{"key":"e_1_2_8_14_3","doi-asserted-by":"publisher","DOI":"10.1523\/JNEUROSCI.5727-07.2008"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b01135"},{"key":"e_1_2_8_15_2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24030601"},{"key":"e_1_2_8_15_3","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(02)00262-7"},{"key":"e_1_2_8_15_4","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.09.117"},{"key":"e_1_2_8_15_5","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1339346"},{"key":"e_1_2_8_15_6","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.03.031"},{"key":"e_1_2_8_15_7","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201500402"},{"key":"e_1_2_8_15_8","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.0c02022"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)01316-A"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)10766-3"},{"key":"e_1_2_8_16_3","doi-asserted-by":"publisher","DOI":"10.1021\/acscombsci.5b00089"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00907"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1034\/j.1399-3011.1999.00049.x"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)01690-0"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1399-3011.2001.00816.x"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1399-3011.1995.tb01065.x"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1034\/j.1399-3011.2002.21018.x"},{"key":"e_1_2_8_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/1099-1387(200006)6:6<264::AID-PSC248>3.0.CO;2-A"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202500836","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,11,7]],"date-time":"2025-11-07T13:52:18Z","timestamp":1762523538000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202500836"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,4,16]]},"references-count":95,"journal-issue":{"issue":"34","published-print":{"date-parts":[[2025,6,17]]}},"alternative-id":["10.1002\/chem.202500836"],"URL":"https:\/\/doi.org\/10.1002\/chem.202500836","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,4,16]]},"assertion":[{"value":"2025-03-06","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-03-11","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-04-16","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202500836"}}