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Azido Glycoside Primer: a Versatile Building Block for the Biocombinatorial Synthesis of Glycosphingolipid Analogues by Maria Carmelita Z Kasuya; Lai X Wang; Yuan C Lee; Motoaki Mitsuki; Hideki Nakajima; Yoshiaki Miura; Toshinori Sato; Kenichi Hatanaka; Sadako Yamagata; Tatsuya Yamagata is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.
What is Azido Glycoside Primer: a Versatile Building Block for the Biocombinatorial Synthesis of Glycosphingolipid Analogues about?
A lactoside primer, 12-azidododecyl b-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 b-lactoside, and an excess of acceptor ensured monoglycosylation of the diol. Mesylation of the v-hydroxyl group in the aglycon, followed by displacement of the mesylate with azide and subsequent O-debenzoylation gave the desired v-azidododecyl b-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 v-azidododecyl b-lactoside primer was 75% of the amount of sialylated n-dodecyl b-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 th
Who reads Azido Glycoside Primer: a Versatile Building Block for the Biocombinatorial Synthesis of Glycosphingolipid Analogues?
It is typically read by researchers, students, and practitioners in Biochemistry, Genetics and Molecular Biology.
- Author
- Maria Carmelita Z Kasuya; Lai X Wang; Yuan C Lee; Motoaki Mitsuki; Hideki Nakajima; Yoshiaki Miura; Toshinori Sato; Kenichi Hatanaka; Sadako Yamagata; Tatsuya Yamagata
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)
- Published
- 2000
- Language
- EN
- Field
- Biochemistry, Genetics and Molecular Biology (Life Sciences)