Chemical one-pot programmable oligosaccharide synthesis
It is readily apparent that enzymes have great utility in glycoconjugate synthesis. In certain cases, complex glyco-structures can be assembled in one pot. However, this is not invariably the case, since enzymatic reaction conditions are not always compatible with one another. Furthermore, enzymes that catalyze every specific desired linkage in a carbohydrate chain are not currently available, and enzymes may also be unpredictable with unnatural structures as substrates. As such, chemical and chemoenzymatic carbohydrate syntheses remain valuable pursuits. If a general reaction condition for chemical glycosylation can be identified, chemical synthesis may be more globally amenable to one-pot strategies. Toward this end, the recently reported one-pot programmable synthesis of oligosaccharides establishes a protocol for the accurate construction of multiple sequential glycosidic bonds. It is hoped that eventually these chemical glycosylation methods will be developed to mirror the specificity of enzyme-catalyzed glycosylation reactions.
Solution-phase chemical methods for one-pot oligosaccharide synthesis have been explored over the past decade by a number of research groups (Raghavan and Kahne, 1993; Ley and Priepke, 1994; Grice et al., 1997). The majority of one-pot synthetic techniques undertaken to date have been largely qualitative. Through various strategies, multiple glycosyl donors have been selected to react in a specific order, thus resulting in a single oligosaccharide product. Techniques identified for the control of glycosyl donor reactivity have included careful selection of hydroxyl protecting groups (Fraser-Reid et al., 1992), manipulation of thioglycoside donor steric bulk (Geurtsen et al., 1997), use of several glycosyl donors of sequentially increasing reactivity (Yamada et al., 1994), or variation of the activating reagent (Chenault and Castro, 1994). An orthogonal protection/deprotection strategy was also reported for the synthesis of an oligosaccharide library, but the extensive time commitment precluded its use as a general practical method (Wong et al., 1998).
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