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The linear rigidity of a 1,3\u2010diynyl linkage provides an optimal distance (7\u2005\u00c5) between \u03b2\u2010carbons of the <jats:italic>i<\/jats:italic>,<jats:italic>i<\/jats:italic>+4 amino acid side chains, thus suggesting its utility in stabilizing \u03b1\u2010helical structures. Here, we report the development of an on\u2010resin strategy for an intramolecular Glaser reaction between two alkyne\u2010terminated side chains by using copper chloride, an essential bpy\u2010diol ligand, and diisopropylethylamine at room temperature. The efficiency of this ligation was illustrated by the synthesis of (<jats:italic>i<\/jats:italic>,<jats:italic>i<\/jats:italic>+4)\u2010, (<jats:italic>i<\/jats:italic>,<jats:italic>i<\/jats:italic>+5)\u2010, (<jats:italic>i<\/jats:italic>,<jats:italic>i<\/jats:italic>+6)\u2010, and (<jats:italic>i<\/jats:italic>,<jats:italic>i<\/jats:italic>+7)\u2010stapled BCL\u20109 \u03b1\u2010helical peptides using the unnatural amino acid propargyl serine. Overall, this procedurally simple method relies on inexpensive and widely available reagents to generate low molecular weight 23\u2010, 26\u2010, 29\u2010, and 32\u2010membered peptide macrocycles.<\/jats:p>","DOI":"10.1002\/cbic.201800121","type":"journal-article","created":{"date-parts":[[2018,3,7]],"date-time":"2018-03-07T21:49:34Z","timestamp":1520459374000},"page":"1031-1035","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":31,"title":["Rigid Peptide Macrocycles from On\u2010Resin Glaser Stapling"],"prefix":"10.1002","volume":"19","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0907-5925","authenticated-orcid":false,"given":"Philip A.","family":"Cistrone","sequence":"first","affiliation":[{"name":"Department of Chemistry The Scripps Research Institute  10550 North Torrey Pines Road La Jolla CA 92037 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anthony P.","family":"Silvestri","sequence":"additional","affiliation":[{"name":"Department of Chemistry The Scripps Research Institute  10550 North Torrey Pines Road La Jolla CA 92037 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jordi C. 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