Azido glycoside primer: A versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues

Maria Carmelita Z Kasuya, Lai X. Wang, Yuan C. Lee, Motoaki Mitsuki, Hideki Nakajima, Yoshiaki Miura, Toshinori Sato, Kenichi Hatanaka, Sadako Yamagata, Tatsuya Yamagata

研究成果: Article

44 引用 (Scopus)

抄録

A lactoside primer, 12-azidododecyl β-lactoside, was synthesized via the Koenigs-Knorr method by glycosylation of 1,12-dodecyldiol with perbenzoylated lactosyl bromide. The presence of the 2-O-acyl substituent in the donor gave the β-lactoside, and an excess of acceptor ensured monoglycosylation of the diol. Mesylation of the ω-hydroxyl group in the aglycon, followed by displacement of the mesylate with azide and subsequent O-debenzoylation gave the desired ω-azidododecyl β-lactoside. The azido glycoside primer was examined in mouse B16 melanoma cells for its feasibility as a building block for oligosaccharide biosynthesis. Uptake of the azido glycoside primer by B16 cells resulted in the sialylation of the galactose residue of the primer to give a glycosylated product having the same glycan as in ganglioside GM3. After 24 h incubation of B16 cells with the primers, the amount of sialylated ω-azidododecyl β-lactoside primer was 75% of the amount of sialylated n-dodecyl β-lactoside. However, after 48 h incubation, both primers gave equal amounts of the sialylated products. Interestingly, the remaining azido glycoside primer after 48 h incubation was 5.6-fold greater than that of the alkyl primer, indicating degradation of the alkyl primer to a larger extent than the ω-azido glycoside primer. The facile chemical synthesis and the efficient uptake in cells make the azido glycoside primer a versatile building block for the biocombinatorial synthesis of glycolipid oligosaccharides.

元の言語English
ページ(範囲)755-763
ページ数9
ジャーナルCarbohydrate Research
329
発行部数4
DOI
出版物ステータスPublished - 2000 12 1
外部発表Yes

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Glycosphingolipids
Glycosides
Oligosaccharides
G(M3) Ganglioside
Glycosylation
Experimental Melanomas
Mesylates
Azides
Glycolipids
Biosynthesis
Bromides
Galactose
Hydroxyl Radical
Polysaccharides
lactosides
Degradation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

これを引用

Kasuya, M. C. Z., Wang, L. X., Lee, Y. C., Mitsuki, M., Nakajima, H., Miura, Y., ... Yamagata, T. (2000). Azido glycoside primer: A versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues. Carbohydrate Research, 329(4), 755-763. https://doi.org/10.1016/S0008-6215(00)00238-X

Azido glycoside primer : A versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues. / Kasuya, Maria Carmelita Z; Wang, Lai X.; Lee, Yuan C.; Mitsuki, Motoaki; Nakajima, Hideki; Miura, Yoshiaki; Sato, Toshinori; Hatanaka, Kenichi; Yamagata, Sadako; Yamagata, Tatsuya.

:: Carbohydrate Research, 巻 329, 番号 4, 01.12.2000, p. 755-763.

研究成果: Article

Kasuya, MCZ, Wang, LX, Lee, YC, Mitsuki, M, Nakajima, H, Miura, Y, Sato, T, Hatanaka, K, Yamagata, S & Yamagata, T 2000, 'Azido glycoside primer: A versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues', Carbohydrate Research, 巻. 329, 番号 4, pp. 755-763. https://doi.org/10.1016/S0008-6215(00)00238-X
Kasuya, Maria Carmelita Z ; Wang, Lai X. ; Lee, Yuan C. ; Mitsuki, Motoaki ; Nakajima, Hideki ; Miura, Yoshiaki ; Sato, Toshinori ; Hatanaka, Kenichi ; Yamagata, Sadako ; Yamagata, Tatsuya. / Azido glycoside primer : A versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues. :: Carbohydrate Research. 2000 ; 巻 329, 番号 4. pp. 755-763.
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title = "Azido glycoside primer: A versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues",
abstract = "A lactoside primer, 12-azidododecyl β-lactoside, was synthesized via the Koenigs-Knorr method by glycosylation of 1,12-dodecyldiol with perbenzoylated lactosyl bromide. The presence of the 2-O-acyl substituent in the donor gave the β-lactoside, and an excess of acceptor ensured monoglycosylation of the diol. Mesylation of the ω-hydroxyl group in the aglycon, followed by displacement of the mesylate with azide and subsequent O-debenzoylation gave the desired ω-azidododecyl β-lactoside. The azido glycoside primer was examined in mouse B16 melanoma cells for its feasibility as a building block for oligosaccharide biosynthesis. Uptake of the azido glycoside primer by B16 cells resulted in the sialylation of the galactose residue of the primer to give a glycosylated product having the same glycan as in ganglioside GM3. After 24 h incubation of B16 cells with the primers, the amount of sialylated ω-azidododecyl β-lactoside primer was 75{\%} of the amount of sialylated n-dodecyl β-lactoside. However, after 48 h incubation, both primers gave equal amounts of the sialylated products. Interestingly, the remaining azido glycoside primer after 48 h incubation was 5.6-fold greater than that of the alkyl primer, indicating degradation of the alkyl primer to a larger extent than the ω-azido glycoside primer. The facile chemical synthesis and the efficient uptake in cells make the azido glycoside primer a versatile building block for the biocombinatorial synthesis of glycolipid oligosaccharides.",
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T2 - A versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues

AU - Kasuya, Maria Carmelita Z

AU - Wang, Lai X.

AU - Lee, Yuan C.

AU - Mitsuki, Motoaki

AU - Nakajima, Hideki

AU - Miura, Yoshiaki

AU - Sato, Toshinori

AU - Hatanaka, Kenichi

AU - Yamagata, Sadako

AU - Yamagata, Tatsuya

PY - 2000/12/1

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N2 - A lactoside primer, 12-azidododecyl β-lactoside, was synthesized via the Koenigs-Knorr method by glycosylation of 1,12-dodecyldiol with perbenzoylated lactosyl bromide. The presence of the 2-O-acyl substituent in the donor gave the β-lactoside, and an excess of acceptor ensured monoglycosylation of the diol. Mesylation of the ω-hydroxyl group in the aglycon, followed by displacement of the mesylate with azide and subsequent O-debenzoylation gave the desired ω-azidododecyl β-lactoside. The azido glycoside primer was examined in mouse B16 melanoma cells for its feasibility as a building block for oligosaccharide biosynthesis. Uptake of the azido glycoside primer by B16 cells resulted in the sialylation of the galactose residue of the primer to give a glycosylated product having the same glycan as in ganglioside GM3. After 24 h incubation of B16 cells with the primers, the amount of sialylated ω-azidododecyl β-lactoside primer was 75% of the amount of sialylated n-dodecyl β-lactoside. However, after 48 h incubation, both primers gave equal amounts of the sialylated products. Interestingly, the remaining azido glycoside primer after 48 h incubation was 5.6-fold greater than that of the alkyl primer, indicating degradation of the alkyl primer to a larger extent than the ω-azido glycoside primer. The facile chemical synthesis and the efficient uptake in cells make the azido glycoside primer a versatile building block for the biocombinatorial synthesis of glycolipid oligosaccharides.

AB - A lactoside primer, 12-azidododecyl β-lactoside, was synthesized via the Koenigs-Knorr method by glycosylation of 1,12-dodecyldiol with perbenzoylated lactosyl bromide. The presence of the 2-O-acyl substituent in the donor gave the β-lactoside, and an excess of acceptor ensured monoglycosylation of the diol. Mesylation of the ω-hydroxyl group in the aglycon, followed by displacement of the mesylate with azide and subsequent O-debenzoylation gave the desired ω-azidododecyl β-lactoside. The azido glycoside primer was examined in mouse B16 melanoma cells for its feasibility as a building block for oligosaccharide biosynthesis. Uptake of the azido glycoside primer by B16 cells resulted in the sialylation of the galactose residue of the primer to give a glycosylated product having the same glycan as in ganglioside GM3. After 24 h incubation of B16 cells with the primers, the amount of sialylated ω-azidododecyl β-lactoside primer was 75% of the amount of sialylated n-dodecyl β-lactoside. However, after 48 h incubation, both primers gave equal amounts of the sialylated products. Interestingly, the remaining azido glycoside primer after 48 h incubation was 5.6-fold greater than that of the alkyl primer, indicating degradation of the alkyl primer to a larger extent than the ω-azido glycoside primer. The facile chemical synthesis and the efficient uptake in cells make the azido glycoside primer a versatile building block for the biocombinatorial synthesis of glycolipid oligosaccharides.

KW - Azido glycoside primer

KW - Lactosyl ceramide analogue

KW - Oligosaccharide library

KW - Oligosaccharides, biocombinatorial synthesis

KW - Saccharide primer, glycosylation

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