Effect of Aglycon Structure on Saccharide Elongation by Cells

• Published in: Chemistry & biodiversity 2015-02, Vol.12 (2), p.239-247
• Main Authors: Kimura, Tamami, Kasuya, Maria Carmelita Z., Hatanaka, Kenichi, Matsuoka, Koji
• Format: Article
• Language: English
• Subjects: Alkyl glycoside primer; Animals; Cell Line, Tumor; Glucosamine - chemistry; Glucosamine - metabolism; Glycolipids - chemistry; Glycolipids - metabolism; Glycosylation; Melanoma, Experimental - metabolism; Melanoma, Experimental - pathology; Mice; Mouse melanoma B16 cells; N-Acetyl-β-D-glucosamine; Oligosaccharides - biosynthesis; Oligosaccharides - chemistry; Saccharide chain elongation
• ISSN: 1612-1872; 1612-1880
• 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.