Open AccessSynthesis of Structurally Defined Nitroxide Spin-Labeled Glycolipids as Useful Probes for Electron Paramagnetic Resonance (EPR) Spectroscopy Studies of Cell Surface Glycans
Author(s) -
Xin Yan,
Zhongwu Guo
Publication year - 2022
Publication title -
synthesis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.885
H-Index - 140
eISSN - 1437-210X
pISSN - 0039-7881
DOI - 10.1055/a-1768-2138
Subject(s) - chemistry , glycan , electron paramagnetic resonance , glycolipid , nitroxide mediated radical polymerization , site directed spin labeling , regioselectivity , combinatorial chemistry , photochemistry , organic chemistry , biochemistry , nuclear magnetic resonance , polymerization , catalysis , glycoprotein , radical polymerization , polymer , physics , membrane
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.