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Novel & Efficient Glycosyl Donors
No.125(March 2007)
Recently, it has been revealed that oligosaccharides are an important factor in the many areas of life processes, such as embryonic growth, differentiation, senescence, immuno system and carcinogenesis. In recognition of the importance of oligosaccharides in bio systems, many have pursued to understand the mechanism of how oligosaccharides play a role in life processes, which requires the need to elucidate the functions of oligosaccharides, as well as the structures and activity relationship. To study the relationship between structures and activity of the oligosaccharides, it is necessary to synthesize oligosaccharides with defind structure so as to evaluate their activity. In the synthesis of oligosaccharides, glycosylation, protection and deprotection processes are repeated for every glycosidic linkage formed. Thus, in order to form oligosaccharides effectively, the glycosyl donor and acceptor, as well as the protecting reagents are vitally important. For this reason, there is much research activity in finding glycosyl donors and acceptors with suitable properties.
In recent years, the glucose derivative 1, with thioformimidate as the leaving group, was developed by Mukaiyama and his co-workers.1) This reagent is a glycosyl donor with high reactivity and stability.
Mukaiyama and his group reported 1b is activated with catalytic amount of TfOH in the presence of MS5A and reacts with a glycosyl acceptor to provide a disaccharide in quantitative yield. Furthermore, by choosing the appropriate solvents, they obtained α- or β-glycosides. The glycosyl acceptors with a fluorine atom at 1-position, as well as the ethylthio group were also used and the resulting disaccharides can also be used as glycosyl donors. Protic acid such as TfOH and Lewis acid such as BF3･Et2O can be used as the activating agents for glycosylation with 1b. Moreover, thiophilic reagents are also compatible. 1b is a white crystalline solid and is attractive because it is easily handled and high reactivity.
References
- 1)Preparation of asparagine-containing glycopeptides
- 2)Synthesis of glycopeptides and oligosaccharides
- 3)Chemo-enzymatic synthesis of bioactive complex glycopeptides
- a)M. Mizuno, K. Haneda, R. Iguchi, I. Muramoto, T. Kawakami, S. Aimoto. K. Yamamoto, T. Inazu, J. Am. Chem. Soc. 1999, 121, 284.
- b)K. Haneda, T. Inazu, K. Yamamoto, Bioscience & Industry 2002, 60, 159.
- a)M. Mizuno, K. Haneda, R. Iguchi, I. Muramoto, T. Kawakami, S. Aimoto. K. Yamamoto, T. Inazu, J. Am. Chem. Soc. 1999, 121, 284.
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TCI has various types of glycosyl derivatives on the market. We are pleased to make these reagents available for your needs in the research of oligosaccharides and related studies. For more information, please refer to "TCI Catalog", "REAGENTS FOR GLYCO-CHEMISTRY AND BIOLOGY" and "Reagent Guide".
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These reagents were merchandised as the fruition of NEDO project. We shall put together further efforts in merchandising effective glycosyl donors and acceptors, and continue to serve the needs of our customers.
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TCI has various types of glycosyl derivatives on the market. We are pleased to make these reagents available for your needs in the research of oligosaccharides and related studies. For more information, please refer to "TCI Catalog", "REAGENTS FOR GLYCO-CHEMISTRY AND BIOLOGY" and "Reagent Guide".
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These reagents were merchandised as the fruition of NEDO project. We shall put together further efforts in merchandising effective glycosyl donors and acceptors, and continue to serve the needs of our customers.
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In addition, sales products changes with areas. Please understand that a product is not available when the product details page is not displayed.