N -Substituted Iminothiolane (NIT): A Promising Strategy for Protecting Lysine Side Chains for Solid-Phase Peptide Chemistry.

Autor:	Aguilar CJ; School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland 1010, New Zealand., Sarwar M; Department of Obstetrics and Gynaecology, University of Otago, Christchurch 8011, New Zealand.; Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, Auckland 1010, New Zealand., Brimble MA; School of Chemical Sciences, and Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3A Symonds Street, Auckland 1010, New Zealand., Kavianinia I; School of Biological Sciences and Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, 3A Symonds Street, Auckland 1010, New Zealand.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2024 Oct 18; Vol. 26 (41), pp. 8922-8927. Date of Electronic Publication: 2024 Oct 09.
DOI:	10.1021/acs.orglett.4c03389
Abstrakt:	In this study, we introduce N -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.
Databáze:	MEDLINE
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