Abstract
Glycolipids are components of the cell membrane capable of transport both from it and in the opposite direction, i.e. from the intercellular matrix to the membrane. The latter opens up the possibility of studying the functioning of glycolipids by their inserting into the cell membrane. In practice, synthetic analogs of glycolipids are significantly more suitable than natural glycolipids for such application, because one can vary properties, modifying their structure, as well as conjugating to other bioactive components, in addition to glycans. This study describes the synthesis of the eight glycolipids containing the same glycan part (A (type 2) tetrasaccharide) but varying in the composition of the lipid part as well as analogs of glycolipids carrying several identical carbohydrate moieties. The resulting series of synthetic analogs of glycolipids opens up the possibility of studying the immunological presentation of the glycan and its recognition by antibodies in the real microenvironment (glycocalyx) of a living cell.
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This study was supported by the Russian Science Foundation (project no. 22-23-00756 “Synthetic glycolipid bioconjugates as instruments for the research of eukaryotic cell”).
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The authors declare that they have no conflicts of interest. This research does not contain any studies involving animals or human participants as objects.
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The article is dedicated to the memory of Academician of the Russian Academy of Sciences Vadim T. Ivanov.
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Abbreviations: Ad, adipoyl; Av, aminovaleric acid; Chol, cholesterol; CMG(2), N-carboxymethylglycine based spacer; DOPE, dioleoylphosphatidylethanolamine; DSPE, distearoylphosphatidylethanolamine; DPyPE, diphytanoylphosphatidylethanolamine; GL, glycolipid; nGL, neoglycolipid.
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Petrakova, D.O., Savchenko, M.S., Popova, I.S. et al. Synthesis of Glycolipid Analogs Containing A (Type 2) Tetrasaccharide. Russ J Bioorg Chem 49, 785–796 (2023). https://doi.org/10.1134/S1068162023040143
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DOI: https://doi.org/10.1134/S1068162023040143