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Effect of Aglycon Structure on Saccharide Elongation by Cells
Author(s) -
Kimura Tamami,
Kasuya Maria Carmelita Z.,
Hatanaka Kenichi,
Matsuoka Koji
Publication year - 2015
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201400278
Subject(s) - chemistry , glycosylation , stereochemistry , elongation , n acetylglucosamine , glycolipid , biochemistry , enzyme , materials science , metallurgy , ultimate tensile strength
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 C 12 to 2 C 6 despite having almost the same number of C‐units.