Recent advances in the glycosylation of sphingosines and ceramides.
Glycosphingolipids (GSLs) are ubiquitous components of eukaryotic cell membranes. They are highly bioactive and are involved in many aspects of cell signalling like cell-cell interaction, cell-substratum interaction and cell-pathogen interaction. GSLs also are involved in the modulation of signal transduction, resulting in regulation of cell proliferation and differentiation. The biological importance and complexity of these compounds afford many opportunities to prepare synthetic analogues for studies of their metabolism in intra- and intercellular processes. This review focuses on recent contributions in the synthesis of GSLs, highlighting improvements in glycosylation reactions leading to alpha and beta glycosyl sphingosines and ceramides and related compounds. Literature from 2000 to the present is covered. The glycosylation reactions leading to the synthesis of GSLs are classified in function of the configuration of the created glycosidic bond (alpha or beta) and of the acceptor used, either azido-sphingosine or ceramide.
Morales-Serna
José Antonio
JA
Departament de Química Analítica i Química Orgànica, Facultat de Química, Universitat Rovira i Virgili, C/Marcelí Domingo s/n, 43005 Tarragona, Spain.
Boutureira
Omar
O
Díaz
Yolanda
Y
Matheu
M Isabel
MI
Castillón
Sergio
S
D002236:Carbohydrate Conformation; D002518:Ceramides / Q000737:chemistry / Q000378:metabolism*; D006027:Glycosides / Q000737:chemistry / Q000378:metabolism*; D006031:Glycosylation; D008958:Models, Molecular; D008968:Molecular Conformation; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D013110:Sphingosine / Q000737:chemistry / Q000378:metabolism*
D002518:Ceramides; D006027:Glycosides; D009844:Oligosaccharides; D013110:Sphingosine