On-Resin Pictet-Spengler Cyclization for 1,2,3,4-Tetrahydro-β-carboline-3-carboxylate (Tcc) Peptide Synthesis With Acid-Labile Functional Tolerance.

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.

SUBMITTER: N'dri OSL 

PROVIDER: S-EPMC12714488 | biostudies-literature | 2026 Feb

REPOSITORIES: biostudies-literature