Synthesis of benzaldehyde-functionalized LewisX trisaccharide analogs for glyco-SAM formation

Silyl-protective groups influencing the reactivity and selectivity in glycosylations

“…In this case an imidate with a 2- O -acetate and 3,4- O -TES protection was used, which ensured stereoselectivity by neighboring-group participation [ 11 ]. For similar reasons the per-TES-protected thioglycoside 7 was employed to prepare the Lewis X trisaccharide: The reaction of 7 with disaccharide 8 promoted by dimethyl disulfide and triflic anhydride gave trisaccharide 9 with high α-selectivity ( Scheme 3 ) [ 12 ]. These conditions, using this promoter system, worked fine in a number of similar cases.…”

Synthesis of l-Hexoses

“…A few l -lactones are commercially available at a reasonable cost and can be turned into highly valuable l -sugars. For instance, peracetylated l -galactose has been prepared by reduction of l -galactono-1,4-lactone 187 followed by peracetylation (Scheme a). ,,, The starting material, l -galactono-1,4-lactone, is a byproduct from the sugar beet industry and is therefore inexpensive and commercially available …”

“…For instance, peracetylated L-galactose has been prepared by reduction of Lgalactono-1,4-lactone 187 followed by peracetylation (Scheme 29a). 49,54,212,213 The starting material, L-galactono-1,4-lactone, is a byproduct from the sugar beet industry and is therefore inexpensive and commercially available. 214 L-Ascorbic acid can be transformed to L-gulono-1,4-lactone and therefore constitutes a potential starting material for the synthesis of L-gulose.…”

“…The l -hexoses have also been used extensively in biomimetics. For instance, l -galactose has been investigated as sialyl-Lewis X (SLe x ) and Lewis X (Le x ) mimetics, − and the mirror image of a blood-type trisaccharide has been prepared . Since it was discovered that some fucosyltransferases can tolerate l -fucose with C6 modifications, a variety of substrates for these enzymes have been developed for various purposes. , For instance, a fluorescently labeled 6-amino-6-deoxy- l -galactose has been used to monitor the activity of the fucosyltransferases, , and incorporation of an azide functionality at C6 on l -fucose has been used as a chemical reporter for imaging fucosylated glycoproteins. , Another topic in which l -sugars are used successfully is neoglycorandomization of drugs like betulinic acid and chlorambucil where the attachment of l -sugars has improved the activity .…”

Glyco-gold nanoparticles: synthesis and applications

“…Carbohydrate–carbohydrate interactions (CCIs), generally characterized by K D values in the millimolar range, are very difficult to detect. Updated data confirm the crucial role of these bindings in the regulation of many cellular processes [ 72 ], however, researches related to the use of carbohydrate-coated gold nanoparticles to investigate CCIs, are still in their infancy and will be not detailed in the present review [ 73 – 74 ]. On the contrary, a vast number of papers reported the use of glyco-gold nanoparticles as smart nanomaterial, able to recognize and interact with proteins, viruses and peptide hormones.…”