(1'R,2'R,3'S)-9-[2'-benzoyloxymethyl-3'-hydroxymethylcyclobutyl]adenine | 207344-94-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1'R,2'R,3'S)-9-[2'-benzoyloxymethyl-3'-hydroxymethylcyclobutyl]adenine
• 英文别名: [(1R,2R,4S)-2-(6-aminopurin-9-yl)-4-(hydroxymethyl)cyclobutyl]methyl benzoate
• CAS: 207344-94-3
• 化学式: C₁₈H₁₉N₅O₃
• 分子量: 353.381
• InChiKey: NTSOLWZOOMDVTI-MGPQQGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1'R,2'R,3'S)-9-[2'-benzoyloxymethyl-3'-hydroxymethylcyclobutyl]adenine 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 (1'R,2'R,3'S)-9-{2'-hydroxymethyl-3'-[bis(p-methoxyphenyl)phenylmethyloxymethyl]cyclobutyl}-N⁶-(N,N-dimethylaminomethylene)adenine
  参考文献：
  名称：

  含碳环氧化苦参素的寡核苷酸的合成与杂交性能

  摘要：

  从具有光学活性的环丁烷衍生物合成含有对映体碳环氧etanocins的寡核苷酸，该对映体具有腺嘌呤，胸腺嘧啶，鸟嘌呤和胞嘧啶。使用熔点法，CD光谱法和混合曲线法（乔布图）研究了它们与互补寡核苷酸的杂交特性。具有腺嘌呤，鸟嘌呤和胞嘧啶碱基的人工核苷酸显示出比脱氧核糖核苷酸更容易与核糖核苷酸形成复合物的趋势。这些复合物是由嘌呤和嘧啶以1：2的比例组成的三链体。在高（1 M NaCl）和低盐（0.1 M NaCl）条件下都观察到了这种三链体的形成。

  DOI：

  10.1016/s0040-4020(00)00162-9
• 作为产物：
  描述：

  (1'S,2'S,3'R)-9-[2',3'-bis(benzoyloxymethyl)cyclobutyl]adenine 在 Lipase MY 作用下， 反应 18.0h， 以10.7%的产率得到(1'R,2'R,3'S)-9-[2'-benzoyloxymethyl-3'-hydroxymethylcyclobutyl]adenine
  参考文献：
  名称：

  High Pressure in Enzyme Catalyzed Organic Reactions

  摘要：

  Adenosine deaminase and lipases catalyzed hydrolysis under high pressure were described. The hydrolysis by both enzymes was facilitated by high pressures. This technique was used for the kinetical resolution of racemic highly modified nucleosides having biological activities.

  DOI：

  10.3987/rev-98-496

文献信息

• Artificial oligonucleotides consisting of an analog of nucleoside antibiotics, carbocyclic oxetanocins
  作者：Nobuya Katagiri、Yoshihiro Morishita、Iichiro Oosawa、Masahiko Yamaguchi

  DOI：10.1016/s0040-4039(99)01410-0

  日期：1999.9

  Modified oligonucleotides, hexadecamers, containing carbocyclic analogues of oxetanocin A and T, have been synthesized from the corresponding chiral carbocyclic nucleosides. The oligonucleotide derived from carbocyclic oxetanocin A forms a stable triple-helix with uridine oligoribonucleotide even under physiological conditions.

  已从相应的手性碳环核苷合成了含有氧杂环丁霉素A和T的碳环类似物的修饰寡核苷酸，六聚体。即使在生理条件下，衍生自碳环氧杂环丁烷素A的寡核苷酸也与尿苷寡核糖核苷酸形成稳定的三螺旋。
• Highly regio- and enantio-selective deacylation of carbocyclic 3′,5′-di-O-acyloxetanocins by lipases
  作者：Nobuya Katagiri、Yoshihiro Morishita、Masahiko Yamaguchi

  DOI：10.1016/s0040-4039(98)00282-2

  日期：1998.4

  Carbocyclic (−)-3′,5′-di-O-acyloxetanocin A and T were hydrolysed by lipase MY to give the corresponding carbocyclic (−)-3′-O-acyloxetanocins with high regioselectivity. Carbocyclic (±)-3′,5′-di-O-acetyloxetanocin A was deacetylated by lipase MY to form the corresponding (±)-3′-O-acetyloxetanocin A with high regioselectivity but with low enantioselectivity whereas the compound when treated with lipase

  碳环（-）-3'，5'-二-O-酰基氧黄霉素A和T被脂肪酶MY水解，得到相应的具有高区域选择性的碳环（-）-3'-O-酰基氧黄霉素。用脂肪酶MY将碳环（±）-3'，5'-二-O-乙酰氧丁酸A脱乙酰化以形成相应的（±）-3'-O-乙酰氧丁酸A，具有较高的区域选择性但对映体选择性低，而该化合物在用XIII型脂肪酶产生具有高区域和对映体选择性的碳环（-）-5'-O-乙酰氧杂环丁烷素A。
• High Pressure in Enzyme Catalyzed Organic Reactions
  作者：Nobuya Katagiri、Masahiko Yamaguchi、Chikara Kaneko

  DOI：10.3987/rev-98-496

  日期：——

  Adenosine deaminase and lipases catalyzed hydrolysis under high pressure were described. The hydrolysis by both enzymes was facilitated by high pressures. This technique was used for the kinetical resolution of racemic highly modified nucleosides having biological activities.
• Synthesis and Hybridization Property of Oligonucleotides Containing Carbocyclic Oxetanocins
  作者：Shinobu Honzawa、Satoshi Ohwada、Yoshihiro Morishita、Kanae Sato、Nobuya Katagiri、Masahiko Yamaguchi

  DOI：10.1016/s0040-4020(00)00162-9

  日期：2000.4

  Oligonucleotides containing enantiomeric carbocyclic oxetanocins possessing adenine, thymine, guanine and cytosine were synthesized from an optically active cyclobutane derivative. Their hybridization properties with the complementary oligonucleotides were studied using melting point method, CD spectroscopy, and mixing curve method (Job plots). The artificial nucleotides possessing adenine, guanine

  从具有光学活性的环丁烷衍生物合成含有对映体碳环氧etanocins的寡核苷酸，该对映体具有腺嘌呤，胸腺嘧啶，鸟嘌呤和胞嘧啶。使用熔点法，CD光谱法和混合曲线法（乔布图）研究了它们与互补寡核苷酸的杂交特性。具有腺嘌呤，鸟嘌呤和胞嘧啶碱基的人工核苷酸显示出比脱氧核糖核苷酸更容易与核糖核苷酸形成复合物的趋势。这些复合物是由嘌呤和嘧啶以1：2的比例组成的三链体。在高（1 M NaCl）和低盐（0.1 M NaCl）条件下都观察到了这种三链体的形成。