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

Hyeok Jun Kwon; Sungduk Gwak; Jun Young Park; Minhaeng Cho; Hogyu Han

doi:10.1021/acsomega.1c04679

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

Hyeok Jun Kwon, Sungduk Gwak, Jun Young Park, Minhaeng Cho, Hogyu Han

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	293-298
Number of pages	6
Journal	ACS Omega
Volume	7
Issue number	1
DOIs	https://doi.org/10.1021/acsomega.1c04679
Publication status	Published - 2022 Jan 11

Bibliographical note

Funding Information:
H.H. is grateful for financial support from the National Research Foundation (NRF) of Korea funded by the Ministry of Science and ICT (NRF2021R1A2C1094754). M.C. thanks financial support from the Institute for Basic Science (IBS-R023-D1). a

Publisher Copyright:
© 2021 The Authors. Published by American Chemical Society

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

Access to Document

10.1021/acsomega.1c04679

Cite this

@article{1f508dfe7ba548058247a6ea0dee5d54,

title = "TfNN15N: A γ-15N-Labeled Diazo-Transfer Reagent for the Synthesis of β-15N-Labeled Azides",

abstract = "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.",

author = "Kwon, {Hyeok Jun} and Sungduk Gwak and Park, {Jun Young} and Minhaeng Cho and Hogyu Han",

note = "Funding Information: H.H. is grateful for financial support from the National Research Foundation (NRF) of Korea funded by the Ministry of Science and ICT (NRF2021R1A2C1094754). M.C. thanks financial support from the Institute for Basic Science (IBS-R023-D1). a Publisher Copyright: {\textcopyright} 2021 The Authors. Published by American Chemical Society",

year = "2022",

month = jan,

day = "11",

doi = "10.1021/acsomega.1c04679",

language = "English",

volume = "7",

pages = "293--298",

journal = "ACS Omega",

issn = "2470-1343",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - TfNN15N

T2 - A γ-15N-Labeled Diazo-Transfer Reagent for the Synthesis of β-15N-Labeled Azides

AU - Kwon, Hyeok Jun

AU - Gwak, Sungduk

AU - Park, Jun Young

AU - Cho, Minhaeng

AU - Han, Hogyu

N1 - Funding Information: H.H. is grateful for financial support from the National Research Foundation (NRF) of Korea funded by the Ministry of Science and ICT (NRF2021R1A2C1094754). M.C. thanks financial support from the Institute for Basic Science (IBS-R023-D1). a Publisher Copyright: © 2021 The Authors. Published by American Chemical Society

PY - 2022/1/11

Y1 - 2022/1/11

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85122745284&partnerID=8YFLogxK

U2 - 10.1021/acsomega.1c04679

DO - 10.1021/acsomega.1c04679

M3 - Article

AN - SCOPUS:85122745284

SN - 2470-1343

VL - 7

SP - 293

EP - 298

JO - ACS Omega

JF - ACS Omega

IS - 1

ER -