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A versatile synthetic route to the preparation of 15 N heterocycles.


ABSTRACT: A robust medium-scale (approximately 3 g) synthetic method for 15 N labeling of pyridine (15 N-Py) is reported based on the Zincke reaction. 15 N enrichment in excess of 81% was achieved with approximately 33% yield. 15 N-Py serves as a standard substrate in a wide range of studies employing a hyperpolarization technique for efficient polarization transfer from parahydrogen to heteronuclei; this technique, called SABRE (signal amplification by reversible exchange), employs a simultaneous chemical exchange of parahydrogen and a to-be-hyperpolarized substrate (e.g., pyridine) on metal centers. In studies aimed at the development of hyperpolarized contrast agents for in vivo molecular imaging, pyridine is often employed either as a model substrate (for hyperpolarization technique development, quality assurance, and phantom imaging studies) or as a co-substrate to facilitate more efficient hyperpolarization of a wide range of emerging contrast agents (e.g., nicotinamide). Here, the produced 15 N-Py was used for the feasibility study of spontaneous 15 N hyperpolarization at high magnetic (HF) fields (7 T and 9.4 T) of an NMR spectrometer and an MRI scanner. SABRE hyperpolarization enabled acquisition of 2D MRI imaging of catalyst-bound 15 N-pyridine with 75 × 75 mm2 field of view (FOV), 32 × 32 matrix size, demonstrating the feasibility of 15 N HF-SABRE molecular imaging with 2.4 × 2.4 mm2 spatial resolution.

SUBMITTER: Chukanov NV 

PROVIDER: S-EPMC6559877 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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A versatile synthetic route to the preparation of <sup>15</sup> N heterocycles.

Chukanov Nikita V NV   Kidd Bryce E BE   Kovtunova Larisa M LM   Bukhtiyarov Valerii I VI   Shchepin Roman V RV   Chekmenev Eduard Y EY   Goodson Boyd M BM   Kovtunov Kirill V KV   Koptyug Igor V IV  

Journal of labelled compounds & radiopharmaceuticals 20190107 13


A robust medium-scale (approximately 3 g) synthetic method for <sup>15</sup> N labeling of pyridine (<sup>15</sup> N-Py) is reported based on the Zincke reaction. <sup>15</sup> N enrichment in excess of 81% was achieved with approximately 33% yield. <sup>15</sup> N-Py serves as a standard substrate in a wide range of studies employing a hyperpolarization technique for efficient polarization transfer from parahydrogen to heteronuclei; this technique, called SABRE (signal amplification by reversib  ...[more]

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