[(2S,5R)-5-(6-氨基-2-氟嘌呤-9-基)四氢呋喃-2-基]甲醇 | 114849-59-1

• 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: [(2S,5R)-5-(6-氨基-2-氟嘌呤-9-基)四氢呋喃-2-基]甲醇
• 英文名称: 2-fluoro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)adenine
• 英文别名: 6-Amino-2-fluoro-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)purine；2-fluoro-2’,3’-dideoxyadenosine；2-Fluoro-2',3'-dideoxyadenosine；[(2S,5R)-5-(6-amino-2-fluoropurin-9-yl)oxolan-2-yl]methanol
• CAS: 114849-59-1
• 化学式: C₁₀H₁₂FN₅O₂
• 分子量: 253.236
• InChiKey: OGSWGOOQBBYAIG-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 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：
  99.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,5R)-5-(6-氨基-2-氟嘌呤-9-基)四氢呋喃-2-基]甲醇 、 甲胺 以 水 为溶剂， 反应 24.0h， 以81%的产率得到6-amino-2-N-methylamino-9-(2,3-dideoxy-β-D-glycero-pentafuranosyl)purine
  参考文献：
  名称：

  Robins, Morris J.; Wilson, John S.; Madej, Danuta, Journal of Heterocyclic Chemistry, 2001, vol. 38, # 6, p. 1297 - 1306

  摘要：

  DOI：
• 作为产物：
  描述：

  2',3'-二脱氧肌苷 在 purine nucleoside 2’-deoxyribosyltransferase from Trypanosoma brucei 作用下， 以 aq. phosphate buffer 为溶剂， 反应 8.0h， 生成 [(2S,5R)-5-(6-氨基-2-氟嘌呤-9-基)四氢呋喃-2-基]甲醇
  参考文献：
  名称：

  使用来自布鲁氏锥虫的高度通用的嘌呤核苷2'-脱氧核糖基转移酶酶促合成治疗性核苷

  摘要：

  与多步化学方法相比，使用酶来合成核苷类似物具有多个优势，包括化学，区域和立体选择性以及较温和的反应条件。本文报道了来自布鲁氏锥虫的嘌呤核苷2'-脱氧核糖基转移酶（PDT）的生产，表征和利用。Tb PDT是一种二聚体，不仅在很宽的温度范围（50–70°C），pH（4–7）和离子强度（0–500 mM NaCl）范围内都显示出出色的活性和稳定性，而且在高温下具有非凡的高稳定性碱性条件（pH 8-10）。bPDT被证明可以熟练地合成许多治疗性核苷，包括去羟肌苷，维达拉滨，克拉屈滨，氟达拉滨和奈拉拉滨。用Ala或Ser进行结构指导的Val11置换，导致变体的活性提高了2.8倍。Tb PDT也共价固定在戊二醛激活的磁性微球上。选择了M Tb PDT3作为最佳衍生物（4200 IU / g，活性回收率为22％），可以轻松地将其重新捕获和再循环用于> 25个反应，而活性损失可忽略不计。最后，男铽PDT3

  DOI：

  10.1002/cctc.201800775

文献信息

• Mutant purine nucleoside phosphorylase proteins and cellular delivery thereof
  申请人：Ealick E. Steven

  公开号：US20050214901A1

  公开（公告）日：2005-09-29

  A host cell stably transformed or transfected by a vector including a DNA sequence encoding for mutant purine nucleoside cleavage enzymes is provided. The transformed or transfected host cell can be used in combination with a purine substrate to treat tumour cells and/or virally infected cells. A nucleotide sequence encoding mutant E. coli derived purine nucleoside phosphorylase proteins which can be used in conjunction with an appropriate substrate to produce toxins which impair abnormal cell growth is also provided. A method is detailed for the delivery of toxin by generation withing target cells or by administration and delivery to the cells from without. Novel purine nucleosides are detailed that yield a cytotoxic purine upn enzymatic cleavage. A synthetic process for nucleosides is also detailed.

  提供了一种由载有突变嘌呤核苷酸裂解酶编码DNA序列的载体转化或转染的宿主细胞。该转化或转染的宿主细胞可与嘌呤底物结合，用于治疗肿瘤细胞和/或病毒感染的细胞。还提供了编码突变E. coli来源的嘌呤核苷酰化酶蛋白的核苷酸序列，可与适当的底物结合使用，产生有害细胞生长的毒素。详细介绍了一种通过靶细胞内生成或通过外部给药和传递给细胞的毒素递送方法。详细介绍了产生细胞毒性嘌呤核苷酶裂解产物的新型嘌呤核苷。还详细介绍了一种核苷的合成过程。
• A highly stereoselective synthesis of anti-HIV 2',3'-dideoxy- and 2',3'-didehydro-2',3'-dideoxynucleosides
  作者：J. Warren Beach、Hea O. Kim、Lak S. Jeong、Satyanarayana Nampalli、Qamrul Islam、Soon K. Ahn、J. Ramesh Babu、Chung K. Chu

  DOI：10.1021/jo00040a031

  日期：1992.7

  A general total synthetic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented. Introduction of an alpha-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give greater-than-or-equal-to 95% beta-isomer. This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine. The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.
• Nucleic Acid-Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogs
  作者：Morris J. Robins、John S. Wilson、Danuta Madej、Nicholas H. Low、Fritz Hansske、Stanislaw F. Wnuk

  DOI：10.1021/jo00129a034

  日期：1995.12

  Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (alpha-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents. Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time. Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino-2-fluoropurine riboside. Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH-) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds. Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides. Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides. A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses. New C-13 NMR data for several types of unsaturated-sugar nucleosides are tabulated. These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.
• ADENOSINE DEAMINASE-STABLE ANTI-RETROVIRAL NUCLEOSIDES
  申请人：SCRIPPS CLINIC AND RESEARCH FOUNDATION

  公开号：EP0355135B1

  公开（公告）日：1993-08-04
• EP0355135A4
  申请人：——

  公开号：EP0355135A4

  公开（公告）日：1990-04-09

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