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晚期碳-14标记与同位素交换:新机遇与未来挑战

Late-Stage Carbon-14 Labeling and Isotope Exchange: Emerging Opportunities and Future Challenges.

作者信息

Babin Victor, Taran Frédéric, Audisio Davide

机构信息

CEA, Département Médicaments et Technologies pour la Santé, SCBM, Université Paris Saclay, 91191 Gif-sur-Yvette, France.

出版信息

JACS Au. 2022 Jun 7;2(6):1234-1251. doi: 10.1021/jacsau.2c00030. eCollection 2022 Jun 27.

DOI:10.1021/jacsau.2c00030
PMID:35783167
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9241029/
Abstract

Carbon-14 (C) is a gold standard technology routinely utilized in pharmaceutical and agrochemical industries for tracking synthetic organic molecules and providing their metabolic and safety profiles. While the state of the art has been dominated for decades by traditional multistep synthetic approaches, the recent emergence of late-stage carbon isotope labeling has provided new avenues to rapidly access carbon-14-labeled biologically relevant compounds. In particular, the development of carbon isotope exchange has represented a fundamental paradigm change, opening the way to unexplored synthetic transformations. In this Perspective, we discuss the recent developments in the field with a critical assessment of the literature. We subsequently discuss research directions and future challenges within this rapidly evolving field.

摘要

碳-14(C)是制药和农用化学品行业常规使用的一种金标准技术,用于追踪合成有机分子并提供其代谢和安全性概况。尽管几十年来传统的多步合成方法一直主导着该领域的技术水平,但最近后期碳同位素标记的出现为快速获取碳-14标记的生物相关化合物提供了新途径。特别是,碳同位素交换的发展代表了一种根本性的范式转变,为未探索的合成转化开辟了道路。在这篇综述中,我们通过对文献的批判性评估来讨论该领域的最新进展。随后,我们讨论了这个快速发展领域的研究方向和未来挑战。

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4
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EJNMMI Radiopharm Chem. 2025 May 30;10(1):27. doi: 10.1186/s41181-025-00346-7.
5
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6
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7
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8
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9
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10
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4
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5
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6
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7
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9
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Nature. 2021 Jan;589(7843):542-547. doi: 10.1038/s41586-020-3015-0. Epub 2020 Nov 25.
10
Carbon isotope labeling of carbamates by late-stage [C], [C] and [C]carbon dioxide incorporation.通过晚期 [C]、[C] 和 [C] 二氧化碳掺入对氨基甲酸酯进行碳同位素标记。
Chem Commun (Camb). 2020 Oct 1;56(78):11677-11680. doi: 10.1039/d0cc05031h.