腺苷-5'-13C | 54447-57-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 腺苷-5'-13C
• 中文别名: 腺苷5′-13C
• 英文名称: [5'-13C]adenosine
• 英文别名: <5'-13C>adenosine；9-β-D-(5'-¹³C)-Ribofuranosyl-adenin；adenosine-5'-13C；(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxy(113C)methyl)oxolane-3,4-diol
• CAS: 54447-57-3
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 268.233
• InChiKey: OIRDTQYFTABQOQ-XUZOCFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  腺苷-5'-13C 在 磺酰氯 作用下， 以 六甲基磷酰三胺 为溶剂， 以67%的产率得到<5'-13C>5'-chloro-5'-deoxyadenosine
  参考文献：
  名称：

  A Convenient and Practical Synthesis of Coenzyme B₁₂Enriched in¹³C in the Cobalt-Bound Carbon

  摘要：

  [A15-C-13]Adenosylcobalamin in which the labeled carbon is bound to the cobalt atom, and its analogs were synthesized from D-[5-C-13]ribose through anomeric hydroxyl activation, coupling with adenosines, and then alkylation of reduced B-12. The synthetic routes described here are mild, efficient, and proceed in reasonable yield.

  DOI：

  10.1080/00397919908086048
• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.75h， 生成 腺苷-5'-13C
  参考文献：
  名称：

  Synthesis of {[A15-13C]5?-deoxy-N1-methyladenosylcobalamin+}Cl?

  摘要：

  The synthesis of {[A15-C-13] 5'-deoxy-N1-methyladenosylcobalamin(+)}Cl-, an analog of coenzyme B-12, was accomplished by glycosidation of [5-C-13]D-ribose with 4-pentenol, followed by benzoylation, coupling to N-6-benzoylaminopurine, deprotection, chlorination at C5', methylation at N1, and oxidative addition to reduced cobalamin. The alpha and beta anomers of the intermediate pent-4-enyl-erythro-furanosides were detected and quantified for the first time.

  DOI：

  10.1002/1099-1344(200006)43:7<635::aid-jlcr348>3.0.co;2-c

文献信息

• A Convenient and Practical Synthesis of Coenzyme B₁₂Enriched in¹³C in the Cobalt-Bound Carbon
  作者：Shifa Cheng、Erie Zang、Kenneth L. Brown

  DOI：10.1080/00397919908086048

  日期：1999.3

  [A15-C-13]Adenosylcobalamin in which the labeled carbon is bound to the cobalt atom, and its analogs were synthesized from D-[5-C-13]ribose through anomeric hydroxyl activation, coupling with adenosines, and then alkylation of reduced B-12. The synthetic routes described here are mild, efficient, and proceed in reasonable yield.
• Synthesis of {[A15-13C]5?-deoxy-N1-methyladenosylcobalamin+}Cl?
  作者：Kenneth L. Brown、Zuping Xia

  DOI：10.1002/1099-1344(200006)43:7<635::aid-jlcr348>3.0.co;2-c

  日期：2000.6

  The synthesis of [A15-C-13] 5'-deoxy-N1-methyladenosylcobalamin(+)}Cl-, an analog of coenzyme B-12, was accomplished by glycosidation of [5-C-13]D-ribose with 4-pentenol, followed by benzoylation, coupling to N-6-benzoylaminopurine, deprotection, chlorination at C5', methylation at N1, and oxidative addition to reduced cobalamin. The alpha and beta anomers of the intermediate pent-4-enyl-erythro-furanosides were detected and quantified for the first time.