Obtaining pure 1H NMR spectra of individual pyranose and furanose anomers of reducing deoxyfluorinated sugars
Obtaining pure 1H NMR spectra of individual pyranose and furanose anomers of reducing deoxyfluorinated sugars
Due to tautomeric equilibria, NMR spectra of reducing sugars can be complex with many overlapping resonances. This hampers coupling constant determination, which is required for conformational analysis and configurational assignment of substituents. Given that mixtures of interconverting species are physically inseparable, easy-to-use techniques that enable facile full 1H NMR characterization of sugars are of interest. Here, we show that individual spectra of both pyranoside and furanoside forms of reducing fluorosugars can be obtained using 1D FESTA. We discuss the unique opportunities offered by FESTA over standard sel-TOCSY and show how it allows a more complete characterization. We illustrate the power of FESTA by presenting the first full NMR characterization of many fluorosugars, including of the important fluorosugar 2-deoxy-2-fluoroglucose. We discuss in detail all practical considerations for setting up FESTA experiments for fluorosugars, which can be extended to any mixture of fluorine-containing species interconverting slowly on the NMR frequency-time scale.
Carbohydrates, Fluorine,Magnetic properties, molecular properties, Quantum mechanics
13908-13925
Poškaitė, Gabija
3ddad395-0937-4eec-ad52-111d9eac0a6b
Wheatley, David E.
259931a5-d5a7-4400-80c9-2a7e8d161a74
Wells, Neil
86312185-007b-495b-86da-4e2e5b9b8025
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Sinnaeve, Davy
1bff7c9e-d706-4318-9042-b291807752d6
6 October 2023
Poškaitė, Gabija
3ddad395-0937-4eec-ad52-111d9eac0a6b
Wheatley, David E.
259931a5-d5a7-4400-80c9-2a7e8d161a74
Wells, Neil
86312185-007b-495b-86da-4e2e5b9b8025
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Sinnaeve, Davy
1bff7c9e-d706-4318-9042-b291807752d6
Poškaitė, Gabija, Wheatley, David E., Wells, Neil, Linclau, Bruno and Sinnaeve, Davy
(2023)
Obtaining pure 1H NMR spectra of individual pyranose and furanose anomers of reducing deoxyfluorinated sugars.
Journal of Organic Chemistry, 88 (19), .
(doi:10.1021/acs.joc.3c01503).
Abstract
Due to tautomeric equilibria, NMR spectra of reducing sugars can be complex with many overlapping resonances. This hampers coupling constant determination, which is required for conformational analysis and configurational assignment of substituents. Given that mixtures of interconverting species are physically inseparable, easy-to-use techniques that enable facile full 1H NMR characterization of sugars are of interest. Here, we show that individual spectra of both pyranoside and furanoside forms of reducing fluorosugars can be obtained using 1D FESTA. We discuss the unique opportunities offered by FESTA over standard sel-TOCSY and show how it allows a more complete characterization. We illustrate the power of FESTA by presenting the first full NMR characterization of many fluorosugars, including of the important fluorosugar 2-deoxy-2-fluoroglucose. We discuss in detail all practical considerations for setting up FESTA experiments for fluorosugars, which can be extended to any mixture of fluorine-containing species interconverting slowly on the NMR frequency-time scale.
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poškaitė-et-al-2023-obtaining-pure-1h-nmr-spectra-of-individual-pyranose-and-furanose-anomers-of-reducing
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e-pub ahead of print date: 27 September 2023
Published date: 6 October 2023
Additional Information:
Funding Information:
This project was funded by the Industrial Biotechnology Catalyst (Innovate UK, BBSRC, EPSRC, BB/M028941/1) to support the translation, development, and commercialization of innovative Industrial Biotechnology processes. We also thank the EPSRC (core capability EP/K039466/1) for funding. G.P. thanks the Southampton Excel programme for a fellowship. Carbosynth and Dextra are thanked for financial support. B.L. acknowledges Research Foundation Flanders (FWO, Belgium) for an Odysseus Type I grant (G0F5621N). The 600 MHz NMR spectrometer in Lille was funded through the CPER CTRL program, cofunded by the European Union (ERDF), the Hauts de France Regional Council (contract #17003781), Métropole Européenne de Lille (contract #2016_ESR_05), and French State (contract #2017-R3-CTRL-Phase 1).
Keywords:
Carbohydrates, Fluorine,Magnetic properties, molecular properties, Quantum mechanics
Identifiers
Local EPrints ID: 483731
URI: http://eprints.soton.ac.uk/id/eprint/483731
ISSN: 0022-3263
PURE UUID: 37186524-d42d-4ce5-bc98-ffe0fa184b91
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Date deposited: 03 Nov 2023 18:02
Last modified: 18 Mar 2024 02:52
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Contributors
Author:
Gabija Poškaitė
Author:
David E. Wheatley
Author:
Davy Sinnaeve
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