2,4-dinitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-deoxy-2-fluoro-β-D-glucopyranoside | 848751-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dinitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-deoxy-2-fluoro-β-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6S)-6-(2,4-dinitrophenoxy)-5-fluoro-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 848751-15-5
• 化学式: C₂₀H₂₆FN₃O₁₄
• 分子量: 551.437
• InChiKey: NMGJBJIERWYSHQ-RKCSWAFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  259
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-3,6-di-O-acetyl-2-deoxy-2-fluoro-D-glucopyranose 在 三乙烯二胺 、 盐酸 、 乙酰氯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 2,4-dinitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-deoxy-2-fluoro-β-D-glucopyranoside
  参考文献：
  名称：

  The chemical synthesis of 2-deoxy-2-fluorodisaccharide probes of the hen egg white lysozyme mechanism

  摘要：

  2,4-Dinitrophenyl 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->4)-2-deoxy-2-fluoro-beta-D-glucopyranoside (GN2FG-DNP) and 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->4)-2-deoxy-2-fluoro-p-D-glucopyranosyl fluoride (GN2FG-F) were prepared using a divergent synthetic approach involving 10 steps. The key steps involved the preparation of 1-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-fluoro-alpha/beta-D-glueopyranose using Selectfluor(TM) in the presence of acetic acid and the subsequent glycosylation of this acceptor to generate the core 2-fluorodisaccharide. After further elaboration, the target molecules were obtained and tested as probes of the mechanism of hen egg white lysozyme (HEWL). Compound GN2FG-DNP is not a substrate for the enzyme while compound GN2FG-F is cleaved slowly with an apparent K., greater than 5 mM and a second-order rate constant of k(cat)/ K-m = 9.6 s(-1) M-1. Comparison of this value to that estimated for the hydrolysis of beta-chitobiosyl fluoride by HEWL (1200 s(-1) M-1) [Ballardie, F. W.; Capon, B.; Cuthbert, M. W.; Dearie, W. M. Bioorg. Chem. 1977, 6, 483-509] revealed a 126-fold rate decrease upon substitution of a fluorine group for the 2-acetamido group of beta-chitobiosyl fluoride. This decrease resulted in the steady-state accumulation of an intermediate as visualized by mass spectrometry and the ultimate crystallographic determination of its structure [Vocadlo, D. J.; Davies, G. J.; Laine, R.; Withers, S. G. Nature 2001, 412, 835-838]. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.12.015