5-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-β-D-arabinofuranosylcytosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-β-D-arabinofuranosylcytosine
• 英文别名: GlcNAc(b1-5)D-Araf(b)-cytosin-1-yl；N-[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₁₇H₂₆N₄O₁₀
• 分子量: 446.414
• InChiKey: PPRODDAGZSJCQZ-ACMLXWNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  217
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  阿糖胞苷 、 4-硝基苯基-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷 反应 24.0h， 生成 5-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-β-D-arabinofuranosylcytosine
  参考文献：
  名称：

  Synthesis of N-Acetylglucosamine-Modified ara-C and Its Effect on Ovarian Cancer Cells

  摘要：

  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.

  DOI：

  10.1021/jm00047a024

文献信息

• Synthesis of N-Acetylglucosamine-Modified ara-C and Its Effect on Ovarian Cancer Cells
  作者：Hiroshi Fujimoto、Tsutomu Takayanagi、Katsumi Ajisaka

  DOI：10.1021/jm00047a024

  日期：1994.10

  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.