“Click” synthesis of monofunctionalized amino- and carboxylic acid-βCDs with low copper(I) catalyst loading

2023 · doi:10.3762/bxiv.2023.67.v1
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This study synthesized monofunctionalized amino- and carboxylic acid-β-cyclodextrin monomers using copper(I)-catalyzed azide-alkyne cycloaddition with low catalyst loading, achieving high yields without chromatography.

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The paper reports the synthesis of monofunctionalized amino- and carboxylic acid β-cyclodextrin monomers starting from mono-6-azido-6-deoxy-β-cyclodextrin using copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC). The authors find that reducing the copper catalyst loading to 1 mol% still yields selectively formed target monomers in high yields, and they avoid chromatographic purification by isolating products through precipitation in acetone, with purity confirmed by 1D NMR. A stated caveat is that the work is presented as a preprint and has not yet been peer reviewed. This paper does not explicitly discuss endometriosis or adenomyosis; it was included in the corpus via a keyword match in the upstream search index.

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Abstract

A series of monofunctionalized amino- and carboxylic acid-β-cyclodextrin monomers were prepared from mono-6-azido-6-deoxy-β-cyclodextrin (N 3 βCD) by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The reduction of copper catalyst to 1 mol% proved to be effective in delivering the desired monomers selectively and in high yields. The use of chromatographic techniques was not needed, as the products were isolated by precipitation in acetone and their purity was confirmed by 1D NMR analyses.
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Materials

chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry A series of monofunctionalized amino- and carboxylic acid-β-cyclodextrin monomers were prepared from mono-6-azido-6-deoxy-β-cyclodextrin (N3βCD) by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The reduction of copper catalyst to 1 mol% proved to be effective in delivering the desired monomers selectively and in high yields. The use of chromatographic techniques was not needed, as the products were isolated by precipitation in acetone and their purity was confirmed by 1D NMR analyses.

Keywords

β-cyclodextrin; cyclodextrin derivatives; click chemistry; CuAAC; mono-functionalization | Format: PDF | Size: 2.3 MB | Download | When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information: D'Andrea, L.; Nielsen, T. T. Beilstein Arch. 2023, 202367. doi:10.3762/bxiv.2023.67.v1 Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below. Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero. © 2023 D'Andrea and Nielsen; licensee Beilstein-Institut. This is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.

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