title: Effect of aglycon structure on saccharide elongation by cells.
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.
authors: 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.
authors: Tamami
authors: T
authors: Kimura
authors: Maria Carmelita Z
authors: MC
authors: Kasuya
authors: Kenichi
authors: K
authors: Hatanaka
authors: Koji
authors: K
authors: Matsuoka
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D005944:Glucosamine / Q000737:chemistry* / Q000378:metabolism; D006017:Glycolipids / Q000737:chemistry* / Q000378:metabolism; D006031:Glycosylation; D008546:Melanoma, Experimental / Q000378:metabolism / Q000473:pathology; D051379:Mice; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000737:chemistry
chemical_list: D006017:Glycolipids; D009844:Oligosaccharides; D005944:Glucosamine
keywords: Alkyl glycoside primer; Mouse melanoma B16 cells; N-Acetyl-β-D-glucosamine; Saccharide chain elongation