5'-azido-5'-deoxy-2',3'-O-isopropylideneguanosine | 25030-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 5'-azido-5'-deoxy-2',3'-O-isopropylideneguanosine
• 英文别名: 5′-azido-5′-deoxy-2′,3′-O-isopropylideneguanosine；2',3'-O-Isopropyliden-5'-azido-5'-desoxy-guanosin；5'-azido-2',3'-O-isopropylideneguanosine；5'-azido-O^2'_,O3'-isopropylidene-5'-deoxy-guanosine；9-[(3aR,4R,6R,6aR)-6-(azidomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-amino-1H-purin-6-one
• CAS: 25030-19-7
• 化学式: C₁₃H₁₆N₈O₄
• 分子量: 348.321
• InChiKey: COFJMICTYLFQLP-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-azido-5'-deoxy-2',3'-O-isopropylideneguanosine 在 吡啶 、 ammonium hydroxide 、 三甲基氯硅烷 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三氟乙酸 作用下， 以 水 、 叔丁醇 为溶剂， 反应 91.0h， 生成 5′-deoxy-(4-(9H-guanin)methyl-1H-1,2,3-triazol-1-yl)guanosine
  参考文献：
  名称：

  Synthesis of Triazole-Linked Analogues of c-di-GMP and Their Interactions with Diguanylate Cyclase

  摘要：

  Cyclic di-GMP (c-di-GMP) is a widespread second messenger that plays a key role in bacterial biofilm formation. The compound's ability to assume multiple conformations allows it to interact with a diverse set of target macromolecules. Here, we analyzed the binding mode of c-di-GMP to the allosteric inhibitory site (I-site) of diguanylate cyclases (DGCs) and compared it to the conformation adopted in the catalytic site of the EAL phosphodiesterases (PDEs). An array of novel molecules has been designed and synthesized by simplifying the native c-di-GMP structure and replacing the charged phosphodiester backbone with an isosteric nonhydrolyzable 1,2,3-triazole moiety. We developed the first neutral small molecule able to selectively target DGCs discriminating between the I-site of DGCs and the active site of PDEs; this molecule represents a novel tool for mechanistic studies, particularly on those proteins bearing both DGC and PDE modules, and for future optimization studies to target DGCs in vivo.

  DOI：

  10.1021/acs.jmedchem.5b01184
• 作为产物：
  描述：

  2',3'-O-异丙亚基鸟苷 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 5'-azido-5'-deoxy-2',3'-O-isopropylideneguanosine
  参考文献：
  名称：

  使用肽支架形成稳定的鸟嘌呤四联体：在水中的H键模式的控制。

  摘要：

  在支架的帮助下：将鸟嘌呤单位预先组织到肽支架上，可以显着稳定G-四重奏基序（见图）。实际上，发现四重奏图案甚至在不添加盐的水中也是稳定的。本研究显示了在这些水性条件下单一合成G-tetrad的首次形成。

  DOI：

  10.1002/chem.201003556

文献信息

• Aryl Fluorosulfate Trapped Staudinger Reduction
  作者：Gerui Ren、Qinheng Zheng、Hua Wang

  DOI：10.1021/acs.orglett.7b00406

  日期：2017.4.7

  A chemoselective Staudinger reduction/sulfur(VI) fluoride exchange cascade has been developed to join two chemical segments through an aryl sulfamate ester (RNH–SO2–OAr) linkage. Aryl fluorosulfate is exploited in this work as the first tetrahedral electrophilic trap for the in situ generated iminophosphorane. Ten examples using azide-containing compounds are presented.

  已开发出化学选择性的Staudinger还原/氟化硫（VI）交换级联反应，可通过氨基磺酸氨基酯（RNH–SO 2 –OAr）键连接两个化学链段。在这项工作中使用了氟代硫酸芳基酯作为第一个四面体亲电阱，用于原位生成的亚氨基正膦。提供了使用含叠氮化物的化合物的十个实例。
• The Use of a Peptidic Scaffold for the Formation of Stable Guanine Tetrads: Control of a H-bonded Pattern in Water
  作者：Pierre Murat、Béatrice Gennaro、Julian Garcia、Nicolas Spinelli、Pascal Dumy、Eric Defrancq

  DOI：10.1002/chem.201003556

  日期：2011.5.16

  With a little help from a scaffold: The pre‐organization of guanine units onto a peptidic scaffold allows a remarkable stabilization of the G‐quartet motif (see graphic). Indeed, the quartet motif was found to be stable even in water without addition of salts. The present study shows the first formation of a single synthetic G‐tetrad under these aqueous conditions.

  在支架的帮助下：将鸟嘌呤单位预先组织到肽支架上，可以显着稳定G-四重奏基序（见图）。实际上，发现四重奏图案甚至在不添加盐的水中也是稳定的。本研究显示了在这些水性条件下单一合成G-tetrad的首次形成。
• A General Synthesis of 5‘-Azido-5‘-deoxy-2‘,3‘-<i>O</i>-isopropylidene Nucleosides
  作者：Fei Liu、David J. Austin

  DOI：10.1021/jo015800m

  日期：2001.12.1
• Template-Assembled Synthetic G-Quartets (TASQs)
  作者：Mehran Nikan、John C. Sherman

  DOI：10.1002/anie.200704199

  日期：2008.6.16
• Synthesis of Triazole-Linked Analogues of c-di-GMP and Their Interactions with Diguanylate Cyclase
  作者：Silvia Fernicola、Ilaria Torquati、Alessandro Paiardini、Giorgio Giardina、Giordano Rampioni、Marco Messina、Livia Leoni、Fabio Del Bello、Riccardo Petrelli、Serena Rinaldo、Loredana Cappellacci、Francesca Cutruzzolà

  DOI：10.1021/acs.jmedchem.5b01184

  日期：2015.10.22

  Cyclic di-GMP (c-di-GMP) is a widespread second messenger that plays a key role in bacterial biofilm formation. The compound's ability to assume multiple conformations allows it to interact with a diverse set of target macromolecules. Here, we analyzed the binding mode of c-di-GMP to the allosteric inhibitory site (I-site) of diguanylate cyclases (DGCs) and compared it to the conformation adopted in the catalytic site of the EAL phosphodiesterases (PDEs). An array of novel molecules has been designed and synthesized by simplifying the native c-di-GMP structure and replacing the charged phosphodiester backbone with an isosteric nonhydrolyzable 1,2,3-triazole moiety. We developed the first neutral small molecule able to selectively target DGCs discriminating between the I-site of DGCs and the active site of PDEs; this molecule represents a novel tool for mechanistic studies, particularly on those proteins bearing both DGC and PDE modules, and for future optimization studies to target DGCs in vivo.