(2R,3S,5R)-5-(3-Benzooxazol-2-yl-2-hydroxy-phenyl)-2-hydroxymethyl-tetrahydro-furan-3-ol | 870181-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2R,3S,5R)-5-(3-Benzooxazol-2-yl-2-hydroxy-phenyl)-2-hydroxymethyl-tetrahydro-furan-3-ol
• CAS: 870181-67-2
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: PATLYBZHBXNINH-NUEKZKHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  95.95
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-5-(3-Benzooxazol-2-yl-2-hydroxy-phenyl)-2-hydroxymethyl-tetrahydro-furan-3-ol 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成
  参考文献：
  名称：

  Differential Solvation and Tautomer Stability of a Model Base Pair within the Minor and Major Grooves of DNA

  摘要：

  2-(2'-Hydroxyphenyl)benzoxazole (HBO) may be used as a model base pair to study solvation, duplex environment, and tautomerization within the major and minor groves of DNA duplexes, In its ground state, HBO possesses an enol moiety which may be oriented syn or anti relative to the imino nitrogen of the benzoxazole ring. In the absence of external hydrogen-bond donors and acceptors HBO exists as the internally hydrogen-bonded syn-enol, a mimic of the rare base pair tautomer found in DNA, which may be photoinduced to tautomerize and form the keto tautomer, a mimic of the dominant base pair tautomer. Previously, we demonstrated that when incorporated into DNA such that the enol moiety is positioned in the major groove, HBO is not solvated, exists exclusively as the internally hydrogen-bonded syn-enol which is efficiently photoinduced to tautomerize, and the corresponding keto tautomer is preferentially stabilized. In stark contrast, we now show that when HBO is incorporated in DNA such that the enol moiety is positioned in the minor groove, the enol tautomer is preferentially stabilized. Molecular dynamics simulations suggest that this results from the formation of a stable hydrogen-bond between the HBO enol and the O4' atom of an adjacent nucleotide, an H-bond acceptor that is only available in the minor groove. The differential stabilization of the enol and keto tautomers in the major and minor grooves may reflect the functions for which these environments evolved, including duplex replication, stability, and recognition.

  DOI：

  10.1021/ja054607x
• 作为产物：
  描述：

  (2R,3S,5R)-5-(3-(benzo[d]oxazol-2-yl)-2-hydroxyphenyl)-2-((benzoyloxy)methyl)tetrahydrofuran-3-yl benzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以76%的产率得到(2R,3S,5R)-5-(3-Benzooxazol-2-yl-2-hydroxy-phenyl)-2-hydroxymethyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  Differential Solvation and Tautomer Stability of a Model Base Pair within the Minor and Major Grooves of DNA

  摘要：

  2-(2'-Hydroxyphenyl)benzoxazole (HBO) may be used as a model base pair to study solvation, duplex environment, and tautomerization within the major and minor groves of DNA duplexes, In its ground state, HBO possesses an enol moiety which may be oriented syn or anti relative to the imino nitrogen of the benzoxazole ring. In the absence of external hydrogen-bond donors and acceptors HBO exists as the internally hydrogen-bonded syn-enol, a mimic of the rare base pair tautomer found in DNA, which may be photoinduced to tautomerize and form the keto tautomer, a mimic of the dominant base pair tautomer. Previously, we demonstrated that when incorporated into DNA such that the enol moiety is positioned in the major groove, HBO is not solvated, exists exclusively as the internally hydrogen-bonded syn-enol which is efficiently photoinduced to tautomerize, and the corresponding keto tautomer is preferentially stabilized. In stark contrast, we now show that when HBO is incorporated in DNA such that the enol moiety is positioned in the minor groove, the enol tautomer is preferentially stabilized. Molecular dynamics simulations suggest that this results from the formation of a stable hydrogen-bond between the HBO enol and the O4' atom of an adjacent nucleotide, an H-bond acceptor that is only available in the minor groove. The differential stabilization of the enol and keto tautomers in the major and minor grooves may reflect the functions for which these environments evolved, including duplex replication, stability, and recognition.

  DOI：

  10.1021/ja054607x