Syntheses of Oligosaccharides Using Cell Function

Sato, Toshinori; Hatanaka, Kenichi; Hashimoto, H.; Yamagata, Toshio

doi:10.4052/tigg.19.1

Cited by 28 publications

(14 citation statements)

References 27 publications

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“…Mouse melanoma B16 cells [24] , African greenmonkey kidney Vero cells [25] and African greenmonkey kidney COS7 cells [26,32] have been used for oligosaccharide production by saccharide primer method. In this regard, mouse melanoma B16 cells sialylated 12-azidododecyl -lactoside into GM3-type oligosaccharide by the action of cellular enzymes (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…3b, the amounts of Gb3-type and Gb4-type oligosaccharide produced by reaction with various numbers of cells were nearly constant and the ratio of the produced oligosaccharides changed according to the reaction condition. When African green-monkey kidney COS7 cells were used for oligosaccharide production by saccharide primer method, GM3-type, GM2-type, GM1-type and GD1a-type oligosaccharides were obtained as described in the literature [26,32] . However, the yield of these products were too low to quantify by HPTLC precisely (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…When African green-monkey kidney Vero cells were used for oligosaccharide production by saccharide primer method, each kind of glycosyltransferase in the cell might act differently under certain reaction conditions. It is generally accepted that the saccharide primer is glycosylated by the same enzyme as in the synthesis of natural glycosphingolipids [32] . In the suspended condition the saccharide primers added in the reaction solution tended to be glycosylated by CMP-sialic acid:LacCer 2-3 sialyltransferase in the African green-monkey kidney Vero cells more easily than UDP-Gal:LacCer 1-4 galactosyltransferase.…”

Section: Discussionmentioning

confidence: 99%

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An Efficient Production of Oligosaccharides by a Reaction using Whole Mammalian Cells as Biocatalysts

Kato¹,

Mitsumori²,

Hatanaka³

2008

American J. of Biochemistry and Biotechnology

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Problem statement: Mammalian cells were used for the production of oligosaccharides by saccharide primer method. However, because cells in culture are used, productivity of oligosaccharides is low. Approach: In saccharide primer method employing cells under culture, glycosylation was performed only by mixing the collected cells in reaction mixtures. Saccharide primer, 12-azidododecyl -lactoside that mimics lactosylceramide (LacCer), was incubated with various mammalian cells under stirring or static conditions. The glycosylated primers were generated by adding and agitating cells in reaction mixtures like in the case where cells in culture were treated with saccharide primer. Results: In the case of African green-monkey kidney (Vero) cells, the amount of generated GM3-type oligosaccharide increased approximately five times by the reaction under agitating condition as compared with the reaction with cells in culture. GM3-type oligosaccharide was also synthesized by mouse melanoma B16 cells under both agitating or standing conditions. Moreover, the amount of GM3-type and GM1-type oligosaccharides produced by using African green-monkey kidney COS7 cells only by mixing the collected cells was greater than the general saccharide primer method. Conclusions/Recommendations:We demonstrated that the suspension mixture of the adhesive cells can be used as a catalyst for the synthesis of oligosaccharides in saccharide primer method. Moreover, suspended cells could produce more amount of oligosaccharides than normally cultured cells.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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An Efficient Production of Oligosaccharides by a Reaction using Whole Mammalian Cells as Biocatalysts

Kato¹,

Mitsumori²,

Hatanaka³

2008

American J. of Biochemistry and Biotechnology

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“…Recently, a novel synthetic method for obtaining oligosaccharide with the functional group was developed [12,13]. In this method, while the cells were cultured in the medium supplemented with the saccharide primer (for example, 12-azidododecyl -lactoside) with the functional group, the saccharide primer was taken into the cells and glycosylated by cellular glycosyltransferases in golgi.…”

Section: Introductionmentioning

confidence: 99%

Development of Membrane Filter with Oligosaccharide Immobilized by Click Chemistry for Influenza Virus Adsorption

Kato¹,

Miyagawa²,

Kasuya³

et al. 2009

TOCBMJ

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Abstract:Membranes with immobilized GM3-type oligosaccharide were prepared and influenza virus adsorption was evaluated. GM3-type oligosaccharide which has azido group in the aglycon was synthesized by saccharide primer method. The azido group was used for combination by click chemistry with alkyne which is introduced to membranes. The position of the azido group in the aglycon of GM3-type oligosaccharide was either the farthest (12-azidododecyl), or the nearest (2-azidododecyl). The azido group in the farthest position showed higher reactivity with alkyne on the membrane than the one in the nearest the GM3-type oligosaccharide. Moreover, the membrane immobilized GM3-type oligosaccharide showed adsorption ability of influenza virus.

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“…Because GM4 is scarce in natural sources, chemical [7 -9] and enzymatic synthetic methods remain to be the conventional strategy for GM4 production in quantitative amounts. However, careful consideration of the synthetic design of GM4 is necessary to overcome the challenges in the regio-and stereoselective incorporation of sialic acid.Recently, we reported the preparation of gangliosides by the saccharide-primer method, a novel strategy, where saccharide primers are used as scaffolds for glycan synthesis in living animal cells [10] [11]. The glycosylation of primers by cellular glycosyltransferases is parallel with the glycosylation of natural precursors and generates products with sequences depending on the biosynthetic pathway of the cell used.…”

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confidence: 99%

Easy Production of a Glycolipid Analogue Using Animal Cells in Culture

Kasuya

Hatanaka

2010

Chemistry & Biodiversity

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A glycolipid analogue, GM4-type ganglioside, was obtained by a combination of chemical synthesis and biosynthetic processes in animal cells with dodecyl beta-D-galactoside (Gal C12) as primer. The primer was conveniently prepared in two steps: glycosylation, followed by deacetylation. The primer was introduced to mouse melanoma B16 cells to serve as substrate for cellular, enzyme-catalyzed glycosylation. Incubation of the cells in the presence of the primer resulted in sialylation of the galactose residue to afford a GM4 analogue that was released from the cells to the culture medium. The strategy of preparation of the GM4 analogue described in this study is a viable alternative to the existing methods. The saccharide-primer method is fast, convenient, not requiring expensive enzymes and glycosyl donors, and highly stereoselective.

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Syntheses of Oligosaccharides Using Cell Function

Cited by 28 publications

References 27 publications

An Efficient Production of Oligosaccharides by a Reaction using Whole Mammalian Cells as Biocatalysts

An Efficient Production of Oligosaccharides by a Reaction using Whole Mammalian Cells as Biocatalysts

Development of Membrane Filter with Oligosaccharide Immobilized by Click Chemistry for Influenza Virus Adsorption

Easy Production of a Glycolipid Analogue Using Animal Cells in Culture

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