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Article

Borylated 5-Membered Ring Iminosugars: Detailed Nuclear Magnetic Resonance Spectroscopic Characterisation, and Method for Analysis of Anomeric and Boron Equilibria

by
Michela Simone
1,2
1
Discipline of Chemistry, University of Newcastle, Callaghan, NSW 2308, Australia
2
Newcastle CSIRO Energy Centre, 10 Murray Dwyer Circuit, Mayfield West, NSW 2304, Australia
Molecules 2025, 30(7), 1402; https://doi.org/10.3390/molecules30071402
Submission received: 28 January 2025 / Revised: 24 February 2025 / Accepted: 25 February 2025 / Published: 21 March 2025
(This article belongs to the Special Issue Applications of NMR Spectroscopy to Problem Solving for Inorganic, Organometallic, and Organic Compounds)
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Abstract

This paper describes the first detailed NMR analysis of the borylated intermediates and target compounds for a small library of pyrrolidine iminosugars of l-gulose absolute stereochemical configuration. The iminosugars were functionalised via N-alkylation to bear a boronate ester or boronic acid groups. The addition of the organic boron pharmacophore allows to further explore the chemical space around and in the active sites, where the boron atom has the capability to make reversible covalent bonds with enzyme nucleophiles and other nucleophiles. We discuss the concurrent complex equilibrium processes of mutarotation and borarotation as studied by NMR.
Keywords: monosaccharide; iminosugar; boronic acid; boronate; boron; BNCT; glycosidase; cancer; Fsp3 index; NMR; mutarotation; borarotation; induced fit monosaccharide; iminosugar; boronic acid; boronate; boron; BNCT; glycosidase; cancer; Fsp3 index; NMR; mutarotation; borarotation; induced fit

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MDPI and ACS Style

Simone, M. Borylated 5-Membered Ring Iminosugars: Detailed Nuclear Magnetic Resonance Spectroscopic Characterisation, and Method for Analysis of Anomeric and Boron Equilibria. Molecules 2025, 30, 1402. https://doi.org/10.3390/molecules30071402

AMA Style

Simone M. Borylated 5-Membered Ring Iminosugars: Detailed Nuclear Magnetic Resonance Spectroscopic Characterisation, and Method for Analysis of Anomeric and Boron Equilibria. Molecules. 2025; 30(7):1402. https://doi.org/10.3390/molecules30071402

Chicago/Turabian Style

Simone, Michela. 2025. "Borylated 5-Membered Ring Iminosugars: Detailed Nuclear Magnetic Resonance Spectroscopic Characterisation, and Method for Analysis of Anomeric and Boron Equilibria" Molecules 30, no. 7: 1402. https://doi.org/10.3390/molecules30071402

APA Style

Simone, M. (2025). Borylated 5-Membered Ring Iminosugars: Detailed Nuclear Magnetic Resonance Spectroscopic Characterisation, and Method for Analysis of Anomeric and Boron Equilibria. Molecules, 30(7), 1402. https://doi.org/10.3390/molecules30071402

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