Borylated 5-Membered Ring Iminosugars: Detailed Nuclear Magnetic Resonance Spectroscopic Characterisation, and Method for Analysis of Anomeric and Boron Equilibria
This paper describes the first detailed NMR analysis of the borylated intermediates and target compounds for a small library of pyrrolidine iminosugars of <span style="font-variant: small-caps;">l</span>-gulose absolute stereochemical configuration. The iminosugars were functio...
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| Main Author: | |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-03-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/7/1402 |
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| Summary: | This paper describes the first detailed NMR analysis of the borylated intermediates and target compounds for a small library of pyrrolidine iminosugars of <span style="font-variant: small-caps;">l</span>-gulose absolute stereochemical configuration. The iminosugars were functionalised via <i>N</i>-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. |
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| ISSN: | 1420-3049 |