Effect of Aglycon Structure on Saccharide Elongation by Cells |
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| Authors: | Tamami Kimura Maria Carmelita Z Kasuya Kenichi Hatanaka Koji Matsuoka |
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| Institution: | 1. Institute of Industrial Science, The University of Tokyo, 4‐6‐1 Komaba, Meguro‐ku, Tokyo 153‐8505, Japan (phone: +81‐3‐54526356);2. Division of Material Science, Graduate School of Science and Engineering, Saitama University, 255 Shimo‐okubo, Sakura‐ku, Saitama 338‐8570, Japan |
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| Abstract: | Alkyl N‐acetyl‐β‐D ‐glucosaminide (GlcNAc primers) with different aglycon moieties were synthesized and used to determine the effect of the aglycon structure on cellular saccharide elongation. Dodecyl N‐acetyl‐β‐D ‐glucosaminide (GlcNAc‐C12), tridecan‐7‐yl N‐acetyl‐β‐D ‐glucosaminide (GlcNAc‐2C6), and pentacosan‐13‐yl N‐acetyl‐β‐D ‐glucosaminide (GlcNAc‐2C12) primers were synthesized by glycosylation of dodecan‐1‐ol, tridecan‐7‐ol, and pentacosan‐13‐ol, respectively, with peracetylglucosamine. These primers were introduced to mouse B16 melanoma cells to prepare glycolipids. After 48 h incubation, results showed that GlcNAc‐C12 was elongated to give NeuAc‐Gal‐GlcNAc‐C12. GlcNAc‐2C6 was also elongated to afford Gal‐GlcNAc‐2C6 and NeuAc‐Gal‐GlcNAc‐2C6. On the other hand, GlcNAc‐2C12 primer was not elongated. Significantly, the results demonstrated that the amount of glycosylated product increased 1.5‐times by modifying the aglycon structure of GlcNAc from C12 to 2 C6 despite having almost the same number of C‐units. |
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| Keywords: | Alkyl glycoside primer Saccharide chain elongation N‐Acetyl‐β ‐D‐glucosamine Mouse melanoma B16 cells |
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