Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation

Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. Despite recent advances in the field, the development of robust and general technologies remains a significant task. This full article reports on a general approach to label urea derivatives with all carbon isotopes, including 14C and 11C. Based on a Staudinger aza-Wittig sequence, it provides access to all aliphatic/aromatic urea combinations as well as to semicarbazides, sulfonylureas, hydroxyl ureas, and simple terminal ureas. A de-risking approach was developed to evaluate the robustness of the reaction. This technology is based on [14C]CO2 screening that allowed to investigate the tolerance of the procedure with most representative heterocycles and functional groups found in FDA approved drugs.

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Robust and General Procedure for Carbon Isotope Labeling of Linear Urea Derivatives with Carbon Dioxide

10.26434/chemrxiv.13519091 ◽

2021 ◽

Author(s):

Victor Babin ◽

Antoine Sallustrau ◽

Olivier Loreau ◽

Fabien Caillé ◽

Amélie Goudet ◽

...

Keyword(s):

Carbon Dioxide ◽

Full Article ◽

Carbon Isotope ◽

Carbon Isotopes ◽

Isotope Labeling ◽

General Procedure ◽

Urea Derivatives ◽

Living Organisms ◽

Approved Drugs ◽

Fda Approved Drugs

Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. Despite recent advances in the field, the development of robust and general technologies remains a significant task. This full article reports on a general approach to label urea derivatives with all carbon isotopes, including 14C and 11C. Based on a Staudinger aza-Wittig sequence, it provides access to all aliphatic/aromatic urea combinations as well as to semicarbazides, sulfonylureas, hydroxyl ureas, and simple terminal ureas. A de-risking approach was developed to evaluate the robustness of the reaction. This technology is based on [14C]CO2 screening that allowed to investigate the tolerance of the procedure with most representative heterocycles and functional groups found in FDA approved drugs.

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Investigation on the Stoichiometry of Carbon Dioxide in Isotope-Exchange Reactions with Phenylacetic Acids

Synlett ◽

10.1055/s-0040-1720447 ◽

2021 ◽

Author(s):

Davide Audisio ◽

Alex Talbot ◽

Antoine Sallustrau ◽

Amélie Goudet ◽

Frédéric Taran

Keyword(s):

Carbon Dioxide ◽

Carbon Isotope ◽

Isotope Exchange ◽

Isotope Labeling ◽

Exchange Reactions ◽

Major Interest ◽

Carbon Dioxide Co2 ◽

Dilution Effects ◽

Product Outcome ◽

Insight Into

AbstractThe functionalization of carbon dioxide (CO2) as a C1 building block has attracted enormous attention. Carboxylation reactions, in particular, are of major interest for applications in isotope labeling. Due to the inexpensive nature of CO2, information about its stoichiometric use is generally unavailable in the literature. Because of the rarity and limited availability of CO2 isotopomers, this parameter is of concern for applications in carbon-isotope labeling. We investigated the effects of the stoichiometry of labeled CO2 on carbon isotope exchange of phenylacetic acids. Both thermal and photocatalytic procedures were studied, providing insight into product outcome and isotope incorporation. Preliminary results on isotope-dilution effects of carbonate bases in photocatalytic carboxylation reactions have also been obtained.

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Response of a continental fault basin to the global OAE1a during the Aptian: Hongmiaozi Basin, Northeast China

Scientific Reports ◽

10.1038/s41598-021-86733-x ◽

2021 ◽

Vol 11 (1) ◽

Author(s):

Daijun Fan ◽

Xuanlong Shan ◽

Yousif M. Makeen ◽

Wentong He ◽

Siyuan Su ◽

...

Keyword(s):

Carbon Dioxide ◽

Carbon Isotope ◽

Carbon Isotopes ◽

Global Climate ◽

Stable Carbon Isotope ◽

Depositional Environments ◽

Carbon Dioxide Partial Pressure ◽

Climate Conditions ◽

Oceanic Anoxic Event ◽

Anoxic Event

AbstractThis paper presents new research on a lacustrine anoxic event (LAE). These data include stable carbon isotope (δ13Corg), pyrite sulfur isotope (δ34Spy), trace element and biomarker ratios from the Hongmiaozi Basin (North China) and unravel the response of continental lakes under the influence of early Aptian extreme climate conditions. According to the stratigraphic chronology (122–118 Ma) and carbon isotope correlations, terrestrial sediment was influenced by the early Aptian Oceanic Anoxic Event (OAE1a). The results show that the Xiahuapidianzi Group experienced a significant warming process under negative excursions in carbon isotopes due to the influence of increased carbon dioxide partial pressure (pCO2). The climate varied from warm and humid to hot and arid (high Sr/Cu, low Rb/Sr, calcareous mudstone), the evaporation and salinity increased (high Sr/Ba and B/Ga), and land input sources decreased (low Zr, Ti and Th). Moreover, high total organic carbon (TOC) content was source from bacteria, algae (n-alkanes), and euxinic depositional environments (Pr/Ph, Cu/Zn and U V Mo). In the stage of continuous carbon isotopes positive excursion, organic matter accumulated rapidly. A paleolake environment model has provided a better understanding of current global climate issues under global warming caused by increased carbon dioxide concentrations.

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General Procedure for Carbon Isotope Labeling of Linear Urea Derivatives with Carbon Dioxide

Chemical Communications ◽

10.1039/d1cc02665h ◽

2021 ◽

Author(s):

Victor Babin ◽

Antoine Sallustrau ◽

Olivier Loreau ◽

Fabien Caillé ◽

Amélie Goudet ◽

...

Keyword(s):

Carbon Dioxide ◽

Carbon Isotope ◽

Organic Compounds ◽

Isotope Labeling ◽

General Procedure ◽

Urea Derivatives ◽

Living Organisms

Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach...

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