Synthesis of sialic acid-lipid conjugates and their neuritogenic effects on N1E.115 neuroblastoma cells

Recent Advances in O-Sialylation

“…This simple glycosylation approach found limited application since it only provides access to unnatural β-sialosides. For example, (methylthio)methyl sialosides could be synthesized by this approach . The method was also applied for the synthesis of methyl glycosides of KDN using either cation-exchange resin (Dowex-50, H + ) , or HCl, formed in situ from AcCl and MeOH .…”

“…It is noteworthy that the C -1 benzyl ester of Neu5Ac gave a higher α-selectivity than those protected as a methyl ester . Other sialyl phosphites −O( n -Bu), −OCH 2 CH 2 Cl, −OCH 2 CCl 3 , −O(CH 2 ) 3 O-, O−CH 2 CH 2 Me 2 CH 2 O-, and 1,2- O -cyclopentyl were found to be less efficient than their OEt or OBn counterparts. However, dimethyl phosphite proved to be rather reactive, especially when promoted with ZnCl 2 /AgClO 4 in CH 2 Cl 2 at room temperature, providing sialosides in high yields (83−85%) and good β-stereoselectivity (α/β 1/5−6) when performed with simple acceptors.…”

Solid-Phase Synthesis of Multiantennary Oligonucleotide Glycoconjugates Utilizing On-Support Oximation

“…The drug molecule may either be noncovalently complexed with a carbohydrate-based carrier or it may be covalently conjugated to an appropriate oligosaccharide construct designed to recognize a given cell-type. For these purposes, a variety of multiantennary glycoclusters (7)(8)(9)(10)(11)(12)(13)(14)(15) glycodendrimers (16)(17)(18), glycopeptides (19), cyclodextrin-based glycoclusters (20,21), and glycopolymers (22)(23)(24)(25) have been synthesized.…”

Catalytic Glycosylations in Oligosaccharide Synthesis

“…After 10 min of stirring, a second acceptor would be added, leading to the desired trisaccharide with two β-glycosidic bonds in a 50% yield. It has also been shown by the Veeneman group that a bicyclic phosphite donor derived from 1,2-cyclopentadiol could be catalytically activated by TfOH . This donor was used for sialylations; however, no sugar acceptors were employed.…”

“…It has also been shown by the Veeneman group that a bicyclic phosphite donor derived from 1,2-cyclopentadiol could be catalytically activated by TfOH. 645 This donor was used for sialylations; however, no sugar acceptors were employed.…”