Peer-reviewed veterinary case report
On-Resin Pictet-Spengler Cyclization for 1,2,3,4-Tetrahydro-β-carboline-3-carboxylate (Tcc) Peptide Synthesis With Acid-Labile Functional Tolerance.
- Year:
- 2026
- Authors:
- N'dri OSL et al.
- Affiliation:
- Département de Chimie · Canada
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.
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Search related cases →Original publication: https://europepmc.org/article/MED/41412558