Kimura Tamami, Kasuya Maria Carmelita Z, Hatanaka Kenichi, Matsuoka Koji
Institute of Industrial Science, The University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan (phone: +81-3-54526356); Division of Material Science, Graduate School of Science and Engineering, Saitama University, 255 Shimo-okubo, Sakura-ku, Saitama 338-8570, Japan.
Chem Biodivers. 2015 Feb;12(2):239-47. doi: 10.1002/cbdv.201400278.
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.
合成了具有不同糖苷配基部分的烷基 N-乙酰基-β-D-葡糖胺（GlcNAc 引物），并用于确定糖苷配基结构对细胞糖类延伸的影响。通过将十二烷-1-醇、十三烷-7-醇和二十五烷-13-醇分别与全乙酰葡糖胺进行糖基化反应，合成了十二烷基 N-乙酰基-β-D-葡糖胺（GlcNAc-C12）、十三烷-7-基 N-乙酰基-β-D-葡糖胺（GlcNAc-2C6）和二十五烷-13-基 N-乙酰基-β-D-葡糖胺（GlcNAc-2C12）引物。将这些引物导入小鼠 B16 黑色素瘤细胞中以制备糖脂。孵育 48 小时后，结果表明 GlcNAc-C12 被延伸生成 NeuAc-Gal-GlcNAc-C12。GlcNAc-2C6 也被延伸得到 Gal-GlcNAc-2C6 和 NeuAc-Gal-GlcNAc-2C6。另一方面，GlcNAc-2C12 引物未被延伸。值得注意的是，结果表明，尽管 C 单元数量几乎相同，但通过将 GlcNAc 的糖苷配基结构从 C12 修改为 2C6，糖基化产物的量增加了 1.5 倍。
