3-(4S-hydroxy-5R-hydroxymethyl-tetrahydro-furan-2R-yl)-pyridine-2,6-dicarboxylic acid dimethyl ester | 316808-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4S-hydroxy-5R-hydroxymethyl-tetrahydro-furan-2R-yl)-pyridine-2,6-dicarboxylic acid dimethyl ester
• CAS: 316808-07-8
• 化学式: C₁₄H₁₇NO₇
• 分子量: 311.291
• InChiKey: FIDJNIJMEGKIGR-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  115.18
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(4S-hydroxy-5R-hydroxymethyl-tetrahydro-furan-2R-yl)-pyridine-2,6-dicarboxylic acid dimethyl ester 在 吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-{5R-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4S-[(2-cyano-ethoxy)-diisipropylamino-phosphanyloxy]-tetrahydro-furan-2R-yl}-pyridine-2,6-dicarboxylic acid dimethyl ester
  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：

  (3-bromo-6-hydroxymethyl-pyridin-2-yl)-methanol 在 吡啶 、 2,6-二甲基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 、 正丁基锂 、 四丁基氟化铵 、 甲基磺酰氯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 phosphate buffer 、 乙醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 14.5h， 生成 3-(4S-hydroxy-5R-hydroxymethyl-tetrahydro-furan-2R-yl)-pyridine-2,6-dicarboxylic acid dimethyl ester
  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