3'-氨基-2',3'-双脱氧鸟苷 | 66323-49-7

• 物质功能分类: 生物化工 - 核苷类药物 - 脱氧核苷酸及其类似物
• 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: 3'-氨基-2',3'-双脱氧鸟苷
• 中文别名: 3’-氨基-2’,3’-双脱氧鸟苷
• 英文名称: 3'-amino-2',3'-dideoxyguanosine
• 英文别名: 3'-Amino-2',3'-dideoxyguanosine；2-amino-9-[(2R,4S,5S)-4-amino-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 66323-49-7
• 化学式: C₁₀H₁₄N₆O₃
• 分子量: 266.26
• InChiKey: HOQBPAWPBCAUGA-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 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：
  141
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-氨基-2',3'-双脱氧鸟苷 在 吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N²-isobutyryl-3'-NH-trityl-2',3'-dideoxyguanosine
  参考文献：
  名称：

  寡核苷酸 N3′⇉P5′ 磷酸酯砌块的新方法

  摘要：

  开发了 3'-氨基核苷的 5'-亚磷酰胺的新合成方法。该方法依赖于使用 3'-amino-2',3'-dideoxy 核苷作为关键起始材料。最终的亚磷酰胺产物是通过 2-3 步高效化学转化获得的，使用选择性地将正交保护基团引入 3'-氨基核苷糖和碱基部分。

  DOI：

  10.1081/ncn-200060068
• 作为产物：
  描述：

  5’-三苯甲基-2’-脱氧-2,3’-双脱氢胸苷 在 吡啶 、 ammonium hydroxide 、 phosphate buffer 、 叠氮化锂 、 cells of E_.coli BMT-38 、 Na-acetate buffer 、 溶剂黄146 、 三苯基膦 作用下， 反应 35.0h， 生成 3'-氨基-2',3'-双脱氧鸟苷
  参考文献：
  名称：

  Chemical-Enzymatic Synthesis of 3′-Amino-2′, 3′-dideoxy-β-D-ribofuranosides of Natural Heterocyclic Bases and Their 5′-Monophosphates

  摘要：

  Treatment of O-2,3'-anhydro-5'-O-trityl derivatives of thymidine (1) and 2'-deoxyuridine (2) with lithium azide in dimethylformamide at 150 degrees C resulted in the formation of the corresponding isomeric 3'-azido-2',3'-dideoxy-5'-O-trityl-beta-D-ribofuranosyl N1- (the major products) and N-3-nucleosides (3/4 and 5/6). 3'-Amino-2',3'-dideoxy-beta-D-ribofuranosides of thymidine [Thd(3'NH2)], uridine [dUrd(3'NH2)], and cytidine [dCyd(3'NH2)] were synthesized from the corresponding 3'-azido derivatives. The Thd(3'NH2) and dUrd(3'NH2) were used as donors of carbohydrate moiety in the reaction of enzymatic transglycosylation of adenine and guanine to afford dAdo(3'NH2) and dGuo(3'NH2). The substrate activity of dN(3'NH2) vs. nucleoside phosphotransferase of the whole cells of Erwinia herbicola was studied.

  DOI：

  10.1080/15257779408013281

文献信息

• Template-Directed Synthesis in 3′- and 5′-Direction with Reversible Termination
  作者：Andreas Kaiser、Sebastian Spies、Tanja Lommel、Clemens Richert

  DOI：10.1002/anie.201203859

  日期：2012.8.13

  Extending both ways: A method for DNA‐templated synthesis on solid support is described. Controlled, stepwise chain extension was demonstrated both in the direction favored by nature (3′‐extension; see scheme) and in the direction typical for conventional DNA synthesizers (5′‐extension).

  两种方法都可以扩展：描述了一种在固相支持物上进行DNA模板合成的方法。在自然界偏爱的方向（3'-延伸；参见方案）和常规DNA合成仪的典型方向（5'-延伸）中都证明了可控的，逐步的链延伸。
• Synthesis of protected 3'-amino nucleoside monomers
  申请人：Gryaznov M. Sergei

  公开号：US20060009636A1

  公开（公告）日：2006-01-12

  Orthogonally protected 3′-amino nucleoside monomers and efficient methods for their synthesis are described. The methods employ selective protection of the 3′-amino group in the presence of the unprotected nucleoside base.

  正交保护的3′-氨基核苷单体及其高效合成方法被描述。这些方法在未保护的核苷碱基存在下，采用对3′-氨基基团的选择性保护。
• Synthesis of all four nucleoside-based β-amino acids as protected precursors for the synthesis of polyamide-DNA with alternating α-amino acid and nucleoside-β-amino acids
  作者：Seema Bagmare、Manojkumar Varada、Anjan Banerjee、Vaijayanti A. Kumar

  DOI：10.1016/j.tet.2012.11.028

  日期：2013.1

  A simple approach is described for the synthesis of all four orthogonally protected nucleoside-β-amino acids from commercially available starting materials. Synthesis of a model tetrameric DNA sequence in 5′–3’direction employing trityl strategy and glycine as α-amino acid alternating with nucleoside-β amino acids is described.

  描述了一种从市售起始原料合成所有四个正交保护的核苷-β-氨基酸的简单方法。描述了使用三苯甲基策略和甘氨酸作为α-氨基酸与核苷-β氨基酸交替的5'-3'方向的模型四聚体DNA序列的合成。
• Method for preparing 3'-amino-2',3'-dideoxyguanosine
  申请人：Seong Ho Dong

  公开号：US20060263859A1

  公开（公告）日：2006-11-23

  Disclosed therein is a method for preparing the 3′-amino-2′,3′-dideoxyguanosine, comprising the steps of: (a) treating 3′-amino-3′-deoxythymidine and 2,6-diaminopurine with a pyrimidine nucleoside phosphorylase and a purine nucleoside phosphorylase to prepare 3′-amino-2′,3′-dideoxyribosyl 2,6-diaminopurine; and (b) converting enzymatically the 3′-amino-2′,3′-dideoxyribosyl 2,6-diaminopurine with an adenosine deaminase to prepare 3′-amino-2′,3′-dideoxyguanosine. According to the present invention, 3′-amino-2′,3′-dideoxyguanosine may be obtained with very high yield in a relatively simple procedure.

  本发明公开了一种制备3'-氨基-2'，3'-二脱氧鸟苷的方法，包括以下步骤：(a)使用嘧啶核苷酸磷酸化酶和嘌呤核苷酸磷酸化酶处理3'-氨基-3'-脱氧胸腺嘧啶和2,6-二氨基嘌呤，制备3'-氨基-2'，3'-二脱氧核糖基2,6-二氨基嘌呤；(b)使用腺苷脱氨酶对3'-氨基-2'，3'-二脱氧核糖基2,6-二氨基嘌呤进行酶促转化，制备3'-氨基-2'，3'-二脱氧鸟苷。根据本发明，可以通过相对简单的程序高产得到3'-氨基-2'，3'-二脱氧鸟苷。
• Biocatalytic synthesis of aminodeoxy purine N9-beta-D-nucleosides containing 3-amino-3-deoxy-beta-D-ribofuranose, 3-amino-2,3-dideoxy-beta-D-ribofuranose, and 2-amino-2-deoxy-beta-D-ribofuranose as sugar moieties
  申请人：Barai N. Vladimir

  公开号：US20070065922A1

  公开（公告）日：2007-03-22

  Purine N 9 -β-D-nucleosides containing 3-amino-3-deoxy-β-D-ribofaranose, 3-amino-2,3-dideoxy-β-D-ribofuranose, and 2-amino-2-deoxy-β-D-ribofuranose as sugar moieties are synthesized by biocatalytic transglycosylation of purine bases and the respective 3′-amino-3′-deoxyuridine, 3′-amino-3′-deoxythymidine and 2′-amino-2′-deoxyuridine as donors of the carbohydrate moiety, and the cells of Escherichia coli as a biocatalyst or glutaraldehyde (GA) treated cells of Escherichia coli as a biocatalyst or a mixture of thymidine (uridine) phosphorylase and purine nucleoside phosphorylase.

  含有3-氨基-3-脱氧-β-D-核糖呋喃糖，3-氨基-2,3-二脱氧-β-D-核糖呋喃糖和2-氨基-2-脱氧-β-D-核糖呋喃糖作为糖基团的嘌呤N9-β-D-核苷酸，通过生物催化转基因嘌呤碱基和相应的3'-氨基-3'-脱氧尿苷、3'-氨基-3'-脱氧胸苷和2'-氨基-2'-脱氧尿苷作为碳水化合物基团供体，以大肠杆菌细胞作为生物催化剂或经戊二醛处理的大肠杆菌细胞作为生物催化剂或胸苷（尿苷）磷酸化酶和嘌呤核苷酸磷酸化酶的混合物进行合成。