Synthesis of N-acetylglucosamine-modified ara-C and its effect on ovarian cancer cells
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H Fujimoto1, T Takayanagi, K Ajisaka
1Meiji Institute of Health Science, Odawara, Japan.
Journal of Medicinal Chemistry
|October 14, 1994
Abstract:
1-beta-D-Arabinofuranosylcytosine (ara-C) was modified by reaction of tetra-N-acetylchitotetraose ((GlcNAc)4) using the transglycosylation activity of thermostable chitinase (EC 3.2.1.14) from Bacillus licheniformis X-7u. The structure of the modified ara-C was determined to be either beta 1-3'- or beta 1-5'-linked GlcNAc-ara-C or (GlcNAc)2-ara-C. The total yield of these glycosylated ara-Cs was about 10%. GlcNAc-ara-C and (GlcNAc)2-ara-C depressed the growth of G-401 cancer cells, while 5-O-beta-D-galactopyranosyl-beta-D-arabinofuranosylcytosine (Gal-ara-C) had no effect on G-401 cells.