Simplifying Oligosaccharide Synthesis:  Efficient Synthesis of Lactosamine and Siaylated Lactosamine Oligosaccharide Donors

Abstract

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Synthesis and Immunological Properties of N-Modified GM3 Antigens as Therapeutic Cancer Vaccines

“…It is worthy pointing out that this is the first synthesis of a glycosylazido derivative of GM3, although a number of procedures for GM3 and other derivatives have been described previously. [33][34][35][36][37][38][39] After 10 was obtained, its trifluoroacetyl group was removed with 0.5 N NaOH solution at room temperature. Under this condition, the hydroxyl and carboxyl groups were also deprotected, but the linker was unaffected.…”

Convenient enzymatic synthesis of a p-nitrophenyl oligosaccharide series of sialyl N-acetyllactosamine, sialyl Lex and relevant compounds

“…In conclusion, a series of pNP sialyl oligosaccharides (9)(10)(11)(12)(13)(14) were synthesized efficiently by combination with b-galactosidase, sialyltransferases and/or fucosyltransferase. These synthetic compounds will be very useful for enzyme kinetic analysis or activity assay, synthesis of artificial glycopolymers and investigation of carbohydrate-mediated biological functions with a surface plasmon resonance technique, a quartz crystal microbalance and other cell-free assay systems.…”

“…In the literature, several synthetic approaches have been proposed to sialyl-N-acetyllactosamine, sLe x and their related derivatives. [8][9][10][11][12] Among them, enzymatic and chemo-enzymatic methods seem to have received increasing attention from the viewpoint of green chemistry. 13 They are advantageous over their chemical counterparts also in terms of efficiency in obtaining the desired oligosaccharides without using protecting groups.…”

Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars

“…Over the years, these and other classes of 2-NHTroc glycosyl donors have been used in glycoside and oligosaccharide synthesis: as trichloroacetimidates, 165,238,258,277, for the synthesis of pyruvated saccharide fragments, 280,304 Lipid A derivatives, 165,281,288,290,294,297,298,305,306 glycopeptides, 277,284,285 lactosaminyl donors, 282,307 Re-type lipopolysaccharides, 289 sialyl Lewis X glycolipids, 291,301 gangliosides, 292 peptidoglycan partial structures, 258,308 thiooligosaccharide analogues 286 of Nod factors, carbohydrate antigens, 295,302 sialyl-trimeric-Lewis X, 300 hyaluronan trisaccharides, 309 meonomycin A analogues, 310 and ceramidated GLA-60 293 derivatives; as fluorides, 282,311,312 for the synthesis of lactosaminyl donors, glycosylamines, 312 and tumor-associated antigen 311 Globo-H; as chlorides; 313 as thioglycosides, 283,286,[314][315][316][317][318][319][320][321][322]…”