| Autor: |
Gwak, Sungduk, Lee, Ji Hye, Kwon, Hyeok-Jun, Han, Hogyu |
| Předmět: |
|
| Zdroj: |
Synlett; Jul2024, Vol. 35 Issue 12, p1429-1435, 7p |
| Abstrakt: |
15 N-Labeled azides have a great potential as practical and effective tags for vibrational probing and hyperpolarized magnetic resonance imaging of biomolecules. They can be synthesized by reaction of primary amines with a15 N-labeled diazo-transfer reagent. TfNN15 N, a γ-15 N-labeled diazo-transfer reagent, was developed to prepare β-15 N-labeled azides; these are vibrational probes devoid of strong spectral interference by Fermi resonance. To overcome the stability and safety problems associated with TfNN15 N, there is a strong demand for the development of a novel γ-15 N-labeled diazo-transfer reagent. We present a study on the diazo-transfer reaction using o -nitrobenzenesulfonyl azide (o -NsN3). o -NsNN15 N, a γ-15 N-labeled diazo-transfer reagent, was newly developed and found to be better than TfNN15 N with respect to its physicochemical properties and ease of synthesis. Unlike TfNN15 N, however, o -NsNN15 N was found to afford a mixture of β- and γ-15 N-labeled azides rather than the β-15 N-labeled azide alone. A mechanism for the diazo-transfer reaction of o -NsNN15 N with primary amines is proposed to explain the formation of such isotopomeric mixtures. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
|
