Aldehyde-catalysed carboxylate exchange in α-amino acids with isotopically labelled CO2

Bsharat, Odey; Doyle, Michael G. J.; Munch, Maxime; Mair, Braeden; Cooze, Christopher; Derdau, Volker; Bauer, Armin; Kong, Deyang; Rotstein, Benjamin H.; Lundgren, Rylan J.

doi:10.1038/s41557-022-01074-0

Cited by 23 publications

(18 citation statements)

References 54 publications

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“…Defluorocarboxylation afforded 13 C-labeled 2a in a good yield with excellent 13 C incorporation (>99% 13 C incorporation), which shows great potential in generating a carbon-labeled version of potentially simple carboxylate prodrug derivatives for subsequent absorption, distribution, metabolism, and excretion (ADME) studies. 22 This result demonstrated that the formate salt acted as the carboxylic source in this defluorocarboxylation reaction. Finally, Stern–Volmer luminescence studies were conducted (Fig.…”

Section: Resultsmentioning

confidence: 78%

Photocatalytic defluorocarboxylation using formate salts as both a reductant and a carbon dioxide source

Min¹,

Song²,

Yan³

et al. 2023

Green Chem.

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Section: Resultsmentioning

confidence: 78%

Photocatalytic defluorocarboxylation using formate salts as both a reductant and a carbon dioxide source

Min¹,

Song²,

Yan³

et al. 2023

Green Chem.

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“…Compounds with 13 C labeling have broad applications in organic chemistry, medicinal chemistry, and life sciences; consequently, catalytic methods enabling site-selective 13 C labeling are of urgent need. − Notably, 13 C-labeled fully substituted pyrroles could be readily synthesized from 13 C-labeled azoalkenes through skeletal recasting (Figure ). Specifically, the 1,3- 13 C-labeled azoalkene 2a′ was easily prepared from 2- 13 C-labeled ethyl acetate in excellent yield, which was then subjected to the reaction with different pyrrole starting materials.…”

Section: Resultsmentioning

confidence: 99%

Molecular Editing of Pyrroles via a Skeletal Recasting Strategy

Zhou,

Huang,

Guo

et al. 2023

ACS Cent. Sci.

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Heterocyclic scaffolds are commonly found in numerous biologically active molecules, therapeutic agents, and agrochemicals. To probe chemical space around heterocycles, many powerful molecular editing strategies have been devised. Versatile C–H functionalization strategies allow for peripheral modifications of heterocyclic motifs, often being specific and taking place at multiple sites. The past few years have seen the quick emergence of exciting “single-atom skeletal editing” strategies, through one-atom deletion or addition, enabling ring contraction/expansion and structural diversification, as well as scaffold hopping. The construction of heterocycles via deconstruction of simple heterocycles is unknown. Herein, we disclose a new molecular editing method which we name the skeletal recasting strategy. Specifically, by tapping on the 1,3-dipolar property of azoalkenes, we recast simple pyrroles to fully substituted pyrroles, through a simple phosphoric acid-promoted one-pot reaction consisting of dearomative deconstruction and rearomative reconstruction steps. The reaction allows for easy access to synthetically challenging tetra-substituted pyrroles which are otherwise difficult to synthesize. Furthermore, we construct N–N axial chirality on our pyrrole products, as well as accomplish a facile synthesis of the anticancer drug, Sutent. The potential application of this method to other heterocycles has also been demonstrated.

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“…In both cases, A m was low, as expected (<0.2 GBq/µmol). A very recent addition to the portfolio of carboxylic acid labelling strategies by isotopic exchange was presented by Bsharat et al [ 33 ]. These authors developed an aldehyde-catalyzed carboxylate exchange reaction in α-amino acids (see Scheme 3 C) with 13 C and 11 C. For the 11 C-reactions, imine carboxylates were pre-formed by condensation of α-amino acids with aryl aldehydes and subsequently subjected to the carboxylate exchange reaction with [ 11 C]CO 2 .…”

Section: Carbon-11 Methodologiesmentioning

confidence: 99%

Recent Developments in Carbon-11 Chemistry and Applications for First-In-Human PET Studies

et al. 2023

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Positron emission tomography (PET) is a molecular imaging technique that makes use of radiolabelled molecules for in vivo evaluation. Carbon-11 is a frequently used radionuclide for the labelling of small molecule PET tracers and can be incorporated into organic molecules without changing their physicochemical properties. While the short half-life of carbon-11 (11C; t½ = 20.4 min) offers other advantages for imaging including multiple PET scans in the same subject on the same day, its use is limited to facilities that have an on-site cyclotron, and the radiochemical transformations are consequently more restrictive. Many researchers have embraced this challenge by discovering novel carbon-11 radiolabelling methodologies to broaden the synthetic versatility of this radionuclide. This review presents new carbon-11 building blocks and radiochemical transformations as well as PET tracers that have advanced to first-in-human studies over the past five years.

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Aldehyde-catalysed carboxylate exchange in α-amino acids with isotopically labelled CO2

Cited by 23 publications

References 54 publications

Photocatalytic defluorocarboxylation using formate salts as both a reductant and a carbon dioxide source

Photocatalytic defluorocarboxylation using formate salts as both a reductant and a carbon dioxide source

Molecular Editing of Pyrroles via a Skeletal Recasting Strategy

Recent Developments in Carbon-11 Chemistry and Applications for First-In-Human PET Studies

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