<1R,2S,3R,4R-(1α,2β,3β,4α)>-D-1,9-dihydro-9-<2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-6H-purin-6-one | 16975-94-3

• 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: <1R,2S,3R,4R-(1α,2β,3β,4α)>-D-1,9-dihydro-9-<2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-6H-purin-6-one
• 英文别名: carbocyclic inosine；adenosine；9-(2,3-dihydroxy-4-hydroxymethyl-cyclopentyl)-1,9-dihydro-purin-6-one；Carbocyclic inosine；9-[(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-1H-purin-6-one
• CAS: 16975-94-3
• 化学式: C₁₁H₁₄N₄O₄
• 分子量: 266.257
• InChiKey: WJJOLBUDGLOYDT-GCXDCGAKSA-N

物化性质

• 沸点：
  695.0±55.0 °C(Predicted)
• 密度：
  1.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  芒霉素 在 adenosine deaminase 作用下， 以 水 为溶剂， 反应 3.0h， 以43.2%的产率得到<1R,2S,3R,4R-(1α,2β,3β,4α)>-D-1,9-dihydro-9-<2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl>-6H-purin-6-one
  参考文献：
  名称：

  通过腺苷脱氨酶的作用拆分嘌呤核苷的外消旋碳环类似物。碳环2'-脱氧鸟苷对映体的抗病毒活性。

  摘要：

  研究了腺苷脱氨酶对6-氨基嘌呤核苷的外消旋碳环类似物的作用。当外消旋碳环腺苷[（+/-）-C-Ado]或外消旋碳环类似物[（+/-）-C-2,6-DAP-2'-dR]为2,6-二氨基嘌呤2'-用该酶孵育脱氧核糖呋喃糖苷，将大约一半的物质快速脱氨基。从所得溶液中，分离出脱氨基碳环类似物的D异构体（D-碳环肌苷，DC-Ino或D-碳环2'-脱氧鸟苷，D-2'-CDG）和未脱碳碳环类似物的L异构体。 。在较高的酶浓度下，LC-Ado和LC-2,6-DAP-2'-dR的脱氨基反应缓慢进行，因此也使其他对映异构体可及。在针对1型和2型单纯疱疹病毒的体外测试中，D-2' -CDG与（+/-）-2'-CDG一样有效，而L-2'-CDG仅显示适度的活性。与先前报道的针对这两种病毒的（+/-）-C-2,6-DAP-2'-dR高活性和效力相反，LC-2,6-DAP-2'-dR没有活性。

  DOI：

  10.1021/jm00387a032

文献信息

• Resolution of racemic carbocyclic analogs of purine nucleosides through the action of adenosine deaminase. Antiviral activity of the carbocyclic 2'-deoxyguanosine enantiomers
  作者：John A. Secrist、John A. Montgomery、Y. Fulmer Shealy、C. Allen O'Dell、Sarah Jo Clayton

  DOI：10.1021/jm00387a032

  日期：1987.4

  The action of adenosine deaminase on racemic carbocyclic analogues of 6-aminopurine nucleosides was investigated. When either racemic carbocyclic adenosine [(+/-)-C-Ado] or the racemic carbocyclic analogue [(+/-)-C-2,6-DAP-2'-dR] of 2,6-diaminopurine 2'-deoxyribofuranoside was incubated with this enzyme, approximately half of the material was deaminated rapidly. From the resulting solution, the D isomers

  研究了腺苷脱氨酶对6-氨基嘌呤核苷的外消旋碳环类似物的作用。当外消旋碳环腺苷[（+/-）-C-Ado]或外消旋碳环类似物[（+/-）-C-2,6-DAP-2'-dR]为2,6-二氨基嘌呤2'-用该酶孵育脱氧核糖呋喃糖苷，将大约一半的物质快速脱氨基。从所得溶液中，分离出脱氨基碳环类似物的D异构体（D-碳环肌苷，DC-Ino或D-碳环2'-脱氧鸟苷，D-2'-CDG）和未脱碳碳环类似物的L异构体。 。在较高的酶浓度下，LC-Ado和LC-2,6-DAP-2'-dR的脱氨基反应缓慢进行，因此也使其他对映异构体可及。在针对1型和2型单纯疱疹病毒的体外测试中，D-2' -CDG与（+/-）-2'-CDG一样有效，而L-2'-CDG仅显示适度的活性。与先前报道的针对这两种病毒的（+/-）-C-2,6-DAP-2'-dR高活性和效力相反，LC-2,6-DAP-2'-dR没有活性。
• Synthesis of Conformationally Restricted Carbocyclic Nucleosides: The Role of the O(4′)-Atom in the Key Hydration Step of Adenosine Deaminase
  作者：Victor E. Marquez、Pamela Russ、Randolph Alonso、Maqbool A. Siddiqui、Susana Hernandez、Clifford George、Marc C. Nicklaus、Fang Dai、Harry Ford, Jr.

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2119::aid-hlca2119>3.0.co;2-y

  日期：1999.12.15
• Conformationally Restricted Nucleosides. The Reaction of Adenosine Deaminase with Substrates Built on a Bicyclo[3.1.0]hexane Template
  作者：Victor E. Marquez、Pamela Russ、Randolph Alonso、Maqbool A. Siddiqui、Kye-Jung Shin、Clifford George、Marc C. Nicklaus、Fang Dai、Harry Ford

  DOI：10.1080/15257779908041487

  日期：1999.4

  Adenosine deaminase (ADA) can discriminate between two distinct (North and South), conformationally rigid substrate conformers. (N)-methanocarba-2'dA (4) is deaminated 100 times faster than the antipodal (S)-methanocarba-2'dA (5), whereas a non-rigid analogue, aristeromycin (6), is deaminated at an intermediate rate. These results are in agreement with crystallographic data from ADA-ribonucleoside complexes showing the furanose ring of the bound purine in a C3'-endo (North) conformation. The data presented here suggests that 4 and 5 are useful probes to ascertain conformational preferences by purine metabolizing enzymes.