<i>N</i>-Substituted Iminothiolane (NIT): A Promising Strategy for Protecting Lysine Side Chains for Solid-Phase Peptide Chemistry
In this study, we introduce <i>N</i>-substituted iminothiolane (NIT) as a robust protecting group for lysine side chains. NIT is compatible with Fmoc-SPPS and can be efficiently removed under mild nucleophilic conditions. Notably, NIT offers enhanced hydrophilicity compared to traditional orthogonal lysine-protecting groups and does not undergo intramolecular migration. Additionally, the synthesis of NIT in aqueous media highlights its eco-friendly nature, positioning it as a promising alternative to protect lysine side chains.
Authors
- Margaret Anne Brimble (ORCID: https://orcid.org/0000-0002-7086-4096)
- Iman Kavianinia (ORCID: https://orcid.org/0000-0002-2446-1376)
- Makhdoom Sarwar (ORCID: https://orcid.org/0000-0003-0030-7785)
- Clouie Justin Aguilar
Institutions
- University of Auckland (NZ)
- Maurice Wilkins Centre (NZ)
- University of Otago (NZ)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-09
- DOI
- https://doi.org/10.1021/acs.orglett.4c03389
- Citations
- 5
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 1.17
Funders
- University of Auckland
- Ministry of Business, Innovation and Employment
- Maurice Wilkins Centre for Molecular Biodiscovery
- Health Research Council of New Zealand