{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["N'dri OSL"],"funding":["Natural Sciences and Engineering Research Council of Canada","Fonds de Recherche du Québec-Nature et Technologie for support of the Biodiversa+ program","Centre in Green Chemistry and Catalysis","CIHR"],"pagination":["e70068"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC12714488"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["32(2)"],"pubmed_abstract":["The constrained tryptophan (Trp) analog 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (Tcc) is used to restrict peptide conformation in structure-activity relationship studies. Although Pictet-Spengler cyclization of Trp and aldehydes with mineral acid gives Tcc analogs, such harsh conditions do not tolerate acid-labile functionality. To enable broader use of Tcc residues, mild conditions are now reported for the on-resin Pictet-Spengler cyclisation in the presence of acid-labile side chain protection and linker strategies."],"journal":["Journal of peptide science : an official publication of the European Peptide Society"],"pubmed_title":["On-Resin Pictet-Spengler Cyclization for 1,2,3,4-Tetrahydro-β-carboline-3-carboxylate (Tcc) Peptide Synthesis With Acid-Labile Functional Tolerance."],"pmcid":["PMC12714488"],"funding_grant_id":["PJT-186296","CGCC, FRQNT-2020-RS4-265155-CCVC","RGPIN-2025-04423","356910"],"pubmed_authors":["Sadanandhan CP","Maclean W","Bhowal KB","Wei X","Truong D","Dif-Yaiche L","Lubell WD","N'dri OSL","Yongo-Luwawa CD","Boccino I","Villeneuve Z"],"additional_accession":[]},"is_claimable":false,"name":"On-Resin Pictet-Spengler Cyclization for 1,2,3,4-Tetrahydro-β-carboline-3-carboxylate (Tcc) Peptide Synthesis With Acid-Labile Functional Tolerance.","description":"The constrained tryptophan (Trp) analog 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (Tcc) is used to restrict peptide conformation in structure-activity relationship studies. Although Pictet-Spengler cyclization of Trp and aldehydes with mineral acid gives Tcc analogs, such harsh conditions do not tolerate acid-labile functionality. To enable broader use of Tcc residues, mild conditions are now reported for the on-resin Pictet-Spengler cyclisation in the presence of acid-labile side chain protection and linker strategies.","dates":{"release":"2026-01-01T00:00:00Z","publication":"2026 Feb","modification":"2026-06-06T05:38:55.125Z","creation":"2026-05-26T03:12:22.707Z"},"accession":"S-EPMC12714488","cross_references":{"pubmed":["41412558"],"doi":["10.1002/psc.70068"]}}