TfNN15N: A γ-15N‑Labeled Diazo-Transfer Reagent for the Synthesis of β-15N‑Labeled Azides

Azides are infrared (IR) probes that are important for structure and dynamics studies of proteins. However, they often display complex IR spectra owing to Fermi resonances and multiple conformers. Isotopic substitution of azides weakens the Fermi resonance, allowing more accurate IR spectral analysi...

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Bibliographic Details
Published in:ACS omega 2022-01, Vol.7 (1), p.293-298
Main Authors: Kwon, Hyeok-Jun, Gwak, Sungduk, Park, Jun Young, Cho, Minhaeng, Han, Hogyu
Format: Article
Language:English
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Summary:Azides are infrared (IR) probes that are important for structure and dynamics studies of proteins. However, they often display complex IR spectra owing to Fermi resonances and multiple conformers. Isotopic substitution of azides weakens the Fermi resonance, allowing more accurate IR spectral analysis. Site-specifically 15N-labeled aromatic azides, but not aliphatic azides, are synthesized through nitrosation. Both 15N-labeled aromatic and aliphatic azides are synthesized through nucleophilic substitution or diazo-transfer reaction but as an isotopomeric mixture. We present the synthesis of TfNN15N, a γ-15N-labeled diazo-transfer reagent, and its use to prepare β-15N-labeled aliphatic as well as aromatic azides.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.1c04679