On‐Resin Pictet–Spengler Cyclization for 1,2,3,4‐Tetrahydro‐β‐carboline‐3‐carboxylate (Tcc) Peptide Synthesis With Acid‐Labile Functional Tolerance
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.
Authors
- Charity D. Yongo‐Luwawa
- Lylia Dif‐Yaiche
- Xiaozheng Wei (ORCID: https://orcid.org/0000-0003-4771-4716)
- William D. Lubell (ORCID: https://orcid.org/0000-0002-3080-2712)
- Darince Truong (ORCID: https://orcid.org/0009-0007-9423-6362)
- Ida Boccino (ORCID: https://orcid.org/0009-0002-6662-007X)
- Kajumee Bora Bhowal (ORCID: https://orcid.org/0009-0001-6154-1746)
- Omer Sayane Landry N'dri (ORCID: https://orcid.org/0009-0006-2372-9656)
- Zoé Villeneuve
- Chitra P. Sadanandhan (ORCID: https://orcid.org/0000-0003-1255-4628)
- Will Maclean
Institutions
- Université de Montréal (CA)
Publication Details
- Journal
- Journal of Peptide Science
- Published
- 2025-12-18
- DOI
- https://doi.org/10.1002/psc.70068
- Primary Topic
- Synthesis and bioactivity of alkaloids
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Centre in Green Chemistry and Catalysis
- Biodiversa+
- Université de Montréal
- Canadian Institutes of Health Research
- Natural Sciences and Engineering Research Council of Canada
- Fonds de recherche du Québec – Nature et technologies