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Synthesis 2022; 54(12): 2856-2864
DOI: 10.1055/a-1768-2138
paper

Synthesis of Structurally Defined Nitroxide Spin-Labeled Glycolipids as Useful Probes for Electron Paramagnetic Resonance (EPR) Spectroscopy Studies of Cell Surface Glycans

Xin Yan 
,
Zhongwu Guo  ∗
This work is partly supported by the National Institute of General Medical Sciences (NIGMS/NIH; R35GM131686). ZG is also grateful to Steven and Rebecca Scott for the endowment. The MS instrument was funded by National Institutes of Health (NIH; S10 OD021758).
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Abstract

Four glycolipids carrying different glycans and a nitroxide free radical spin at the glycan non-reducing end were designed and synthesized from free glucose and maltooligosaccharides by an efficient and streamlined synthetic strategy. The main features of this synthetic strategy include regioselective functionalization of the free carbohydrates and coupling of the radical spin label with functionalized free glycans as the last synthetic step. These glycolipids are useful probes for the study of cell surface glycans by electron paramagnetic resonance spectroscopy. Moreover, the key synthetic intermediates, free glycolipids carrying a flexible azido group at the glycan non-reducing end, are widely useful platforms for accessing glycolipids with other molecular labels.

Key words

glycolipids - carbohydrates - glycans - nitroxides - radical spin label - electron paramagnetic resonance spectroscopy

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1768-2138.
  • Supporting Information


Publication History

Received: 14 December 2021

Accepted after revision: 10 February 2022

Accepted Manuscript online:
10 February 2022

Article published online:
04 April 2022

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