{6-hydroxymethyl-3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxy-methyl)-tetrahydro-furan-2R-yl]-pyridin-2-yl}-methanol | 316808-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {6-hydroxymethyl-3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxy-methyl)-tetrahydro-furan-2R-yl]-pyridin-2-yl}-methanol
• CAS: 316808-04-5
• 化学式: C₂₈H₃₃NO₇
• 分子量: 495.573
• InChiKey: PXJQKISSOOGZQD-OZNIXHKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  99.5
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  {6-hydroxymethyl-3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxy-methyl)-tetrahydro-furan-2R-yl]-pyridin-2-yl}-methanol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 作用下， 以 phosphate buffer 、 乙腈 为溶剂， 以1.58 g的产率得到3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2R-yl]-pyridine-2,6-dicarboxylic acid
  参考文献：
  名称：

  A second-generation copper(II)-mediated metallo-DNA-base pair

  摘要：

  Metal-dependent pairing of nucleobases represents an alternative DNA base pairing scheme. Our first-generation copper(II)-mediated pyridine-2,6-dicarboxylate (Dipic) and pyridine (Py) metallo-base pair has a stability comparable to the natural base pairs dA:dT and dC:dG but does not have the selectivity of the Watson Crick base pairs. In order to increase the selectivity of base pair formation, a second-generation metallo-base pair was generated consisting of a pyridine-2,6-dicarboxamide (Dipam) and a pyridine (Py) nucleobase. This new metallo-base pair is more stable than the natural base pairs dA:dT and dC:dG and highly selective against mispairing. In addition, incorporation of multiple metallo-base pairs into DNA results in the formation of stable duplexes demonstrating that hydrogen bonding base pairs can efficiently be replaced by metal-dependent base pairs at multiple sites in DNA. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2003.09.001
• 作为产物：
  描述：

  2,6-bis-(tetr-butyl-dimethyl-silanyloxymethyl)-3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxy-methyl)-tetrahydro-furan-2R-yl]-pyridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以98%的产率得到{6-hydroxymethyl-3-[4S-(4-methoxy-benzyloxy)-5R-(4-methoxy-benzyloxy-methyl)-tetrahydro-furan-2R-yl]-pyridin-2-yl}-methanol
  参考文献：
  名称：

  A second-generation copper(II)-mediated metallo-DNA-base pair

  摘要：

  Metal-dependent pairing of nucleobases represents an alternative DNA base pairing scheme. Our first-generation copper(II)-mediated pyridine-2,6-dicarboxylate (Dipic) and pyridine (Py) metallo-base pair has a stability comparable to the natural base pairs dA:dT and dC:dG but does not have the selectivity of the Watson Crick base pairs. In order to increase the selectivity of base pair formation, a second-generation metallo-base pair was generated consisting of a pyridine-2,6-dicarboxamide (Dipam) and a pyridine (Py) nucleobase. This new metallo-base pair is more stable than the natural base pairs dA:dT and dC:dG and highly selective against mispairing. In addition, incorporation of multiple metallo-base pairs into DNA results in the formation of stable duplexes demonstrating that hydrogen bonding base pairs can efficiently be replaced by metal-dependent base pairs at multiple sites in DNA. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2003.09.001

文献信息

• A Novel Silver(I)-Mediated DNA Base Pair
  作者：Nicole Zimmermann、Eric Meggers、Peter G. Schultz

  DOI：10.1021/ja0279951

  日期：2002.11.1

  generated a novel silver(I)-mediated unnatural DNA base pair consisting of two 2,6-bis(ethylthiomethyl)pyridine nucleobases SPy. This metallo-base pair has a remarkably high pairing stability and selectivity which rivals that of the natural base pairs dA:dT and dC:dG. UV-melting experiments revealed that the dSPy:dSPy self-pair can replace natural base pairs at multiple sites and still form stable DNA duplexes

  我们已经生成了一种新型的银 (I) 介导的非天然 DNA 碱基对，由两个 2,6-双（乙硫基甲基）吡啶核碱基 SPy 组成。这种金属碱基对具有非常高的配对稳定性和选择性，可与天然碱基对 dA:dT 和 dC:dG 相媲美。紫外熔解实验表明 dSPy:dSPy 自对可以在多个位点替换天然碱基对，并仍然形成稳定的 DNA 双链体。