<i>N</i>‑Substituted Iminothiolane\n(NIT): A Promising Strategy for Protecting Lysine Side Chains for\nSolid-Phase Peptide Chemistry

In this study, we introduce <i>N</i>-substituted\niminothiolane\n(NIT) as a robust protecting group for lysine side chains. NIT is\ncompatible with Fmoc-SPPS and can be efficiently removed under mild\nnucleophilic conditions. Notably, NIT offers enhanced hydrophilicity\ncompared to traditional orthogonal lysine-protecting groups and does\nnot undergo intramolecular migration. Additionally, the synthesis\nof NIT in aqueous media highlights its eco-friendly nature, positioning\nit as a promising alternative to protect lysine side chains.

Publication Details

Journal
Figshare
Published
2024-10-09
DOI
https://doi.org/10.1021/acs.orglett.4c03389.s001
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
0.00
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article

N‑Substituted Iminothiolane\n(NIT): A Promising Strategy for Protecting Lysine Side Chains for\nSolid-Phase Peptide Chemistry

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Chemical Synthesis and Analysis
article

N‑Substituted Iminothiolane\n(NIT): A Promising Strategy for Protecting Lysine Side Chains for\nSolid-Phase Peptide Chemistry

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Abstract

In this study, we introduce <i>N</i>-substituted\niminothiolane\n(NIT) as a robust protecting group for lysine side chains. NIT is\ncompatible with Fmoc-SPPS and can be efficiently removed under mild\nnucleophilic conditions. Notably, NIT offers enhanced hydrophilicity\ncompared to traditional orthogonal lysine-protecting groups and does\nnot undergo intramolecular migration. Additionally, the synthesis\nof NIT in aqueous media highlights its eco-friendly nature, positioning\nit as a promising alternative to protect lysine side chains.

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Openalex Percentile: Top 76%
Chemical Synthesis and Analysis
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<i>N</i>‑Substituted Iminothiolane\n(NIT): A Promising Strategy for Protecting Lysine Side Chains for\nSolid-Phase Peptide Chemistry · Figshare (2024) | TGRS Research Map | TGRS