Kwon Hyeok-Jun, Gwak Sungduk, Park Jun Young, Cho Minhaeng, Han Hogyu
Department of Chemistry, Korea University, Seoul 02841, Korea.
Center for Molecular Spectroscopy and Dynamics, Institute for Basic Science (IBS), Seoul 02841, Korea.
ACS Omega. 2021 Dec 30;7(1):293-298. doi: 10.1021/acsomega.1c04679. eCollection 2022 Jan 11.
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 N-labeled aromatic azides, but not aliphatic azides, are synthesized through nitrosation. Both N-labeled aromatic and aliphatic azides are synthesized through nucleophilic substitution or diazo-transfer reaction but as an isotopomeric mixture. We present the synthesis of TfNNN, a γ-N-labeled diazo-transfer reagent, and its use to prepare β-N-labeled aliphatic as well as aromatic azides.
叠氮化物是红外（IR）探针，对蛋白质的结构和动力学研究很重要。然而，由于费米共振和多种构象异构体，它们常常呈现出复杂的红外光谱。叠氮化物的同位素取代减弱了费米共振，从而实现更准确的红外光谱分析。通过亚硝化反应可位点特异性地合成N标记的芳香族叠氮化物，但不能合成脂肪族叠氮化物。N标记的芳香族和脂肪族叠氮化物均可通过亲核取代或重氮转移反应合成，但会形成同位素异构体混合物。我们展示了γ-N标记的重氮转移试剂TfNNN的合成及其用于制备β-N标记的脂肪族和芳香族叠氮化物的用途。
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