{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T16:35:55Z","timestamp":1786725355758,"version":"build-2736575974"},"reference-count":60,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2026,8,9]],"date-time":"2026-08-09T00:00:00Z","timestamp":1786233600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,8,9]],"date-time":"2026-08-09T00:00:00Z","timestamp":1786233600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","award":["RGPIN\u20102020\u201003894"],"award-info":[{"award-number":["RGPIN\u20102020\u201003894"]}],"id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2026,8,14]]},"abstract":"<jats:p>\n                    Microcin J25 (MccJ25) is of special interest due to its \u201clariat\u201d topology. The lasso architecture is thought to be responsible for its remarkable thermal stability (100\u00b0C for 30\u2009min incubation) and potency against Gram\u2010negative bacteria (i.e., MBC of ~4.75\u2009\u00b5M against\n                    <jats:italic>E. coli<\/jats:italic>\n                    strain DH5\u03b1). This naturally occurring lasso peptide is formed via post\u2010translational modifications (PTMs), including leader peptide removal and macrolactam cyclization between the N\u2010terminus and 8\u2010Glu side chain. Since the discovery of MccJ25 in 1992, synthetic endeavors toward the total chemical synthesis of MccJ25 have remained elusive. Herein, we investigated the chemical synthesis of MccJ25 utilizing \u03b2\u2010thiol amino acids as the chemical tools to prestaple and rigidify the peptide backbone through disulfide linkages. Although the proposed chemical strategy failed to afford the desired lasso configuration, synthetic routes toward Fmoc\u2010SPPS compatible, stereoselective \u03b2\u2010thiol amino acids via thiazoline derivatives were developed. In addition, chemical\/biochemical literature synthesis of MccJ25 and its analogs, as well as the synthesis of \u03b2\u2010thiol amino acids, are summarized within.\n                  <\/jats:p>","DOI":"10.1002\/cbic.70452","type":"journal-article","created":{"date-parts":[[2026,8,9]],"date-time":"2026-08-09T11:09:54Z","timestamp":1786273794000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of \u03b2\u2010Thiolated Amino Acids: Investigation Toward the Total Chemical Synthesis of Lasso Peptide Microcin J25"],"prefix":"10.1002","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0009-0006-4445-3871","authenticated-orcid":false,"given":"Yu\u2010Ting","family":"Hsiao","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Alberta  Edmonton Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5014-3251","authenticated-orcid":false,"given":"Bethan L.","family":"Heard","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Alberta  Edmonton Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ilia","family":"Perov","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Alberta  Edmonton Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9296-6069","authenticated-orcid":false,"given":"Marco J.","family":"van Belkum","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Alberta  Edmonton Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sorina","family":"Chiorean","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Alberta  Edmonton 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