Synthetic Strategies for Modified Glycosphingolipids and Their Design as Probes
| Autor: | Gour Chand Daskhan, Michele R. Richards, Christopher W. Cairo, Tianlin Guo, Carmanah D. Hunter |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Glycan
Glycosylation Fluorophore Glycoside Hydrolases Chemistry Techniques Synthetic Computational biology 010402 general chemistry 01 natural sciences Glycosphingolipids Cell membrane chemistry.chemical_compound Glycolipid Carbohydrate Conformation medicine biology 010405 organic chemistry Chemistry Glycosyltransferases General Chemistry Semisynthesis 0104 chemical sciences medicine.anatomical_structure Molecular Probes biology.protein lipids (amino acids peptides and proteins) Bioorthogonal chemistry |
| Zdroj: | Chemical Reviews. 118:8188-8241 |
| ISSN: | 1520-6890 0009-2665 |
| DOI: | 10.1021/acs.chemrev.8b00070 |
| Popis: | The plasma membrane of cells contains a diverse array of lipids that provide important structural and biological features. Glycolipids are typically a minor component of the cell membrane and consist primarily of glycosphingolipids (GSLs). GSLs in vertebrates contain a multifarious assortment of glycan headgroups, which can be important to biological functions based on lipid-lipid and lipid-protein interactions. The design of probes to study these complex targets requires advanced synthetic methodologies. In this Review, we will discuss recent advances in chemical and chemoenzymatic synthesis of GSLs in conjunction with the use of these approaches to design new probes. Examples using either chemical or enzymatic semisynthesis methods starting from isolated GSLs will also be reviewed. Focusing primarily on vertebrate glycolipids, we will highlight examples of radionuclide, fluorophore, photoresponsive, and bioorthogonal tagged GSL probes. |
| Databáze: | OpenAIRE |
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