乙基3,4,5-三[[(6-重氮基-5,6-二氢-5-羰基-1-萘基)磺基基]氧代]苯酸酯 | 73120-97-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 中文名称: 乙基3,4,5-三[[(6-重氮基-5,6-二氢-5-羰基-1-萘基)磺基基]氧代]苯酸酯
• 中文别名: 环二((3'-5')尿甙酸)
• 英文名称: c(UU)
• 英文别名: cy-rUU；3',3'-cdUMP；cyclic di-UMP；Cyclisches Uridin-dinucleotid；cyclo-[uridylyl-(5'->3')-uridylyl-(5'->3')]；Cyclic bis((3'-5')uridylic acid)；1-[(1S,6R,8R,9R,10S,15R,17R,18R)-17-(2,4-dioxopyrimidin-1-yl)-3,9,12,18-tetrahydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.3.0.06,10]octadecan-8-yl]pyrimidine-2,4-dione
• CAS: 73120-97-5
• 化学式: C₁₈H₂₂N₄O₁₆P₂
• 分子量: 612.337
• InChiKey: ADHSUZMEJHOWOL-NCOIDOBVSA-N

物化性质

• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.9
• 重原子数：
  40
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  269
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  乙基3,4,5-三[[(6-重氮基-5,6-二氢-5-羰基-1-萘基)磺基基]氧代]苯酸酯 在 ammonium acetate 作用下， 生成
  参考文献：
  名称：

  Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase

  摘要：

  Five analogs of cyclic di-nucleotidic acid including c-di-GMP were synthesized and evaluated for their biological activities on Slr1143, a diguanylate cyclase of Synechocystis sp. Slr1143 was overexpressed from the recombinant plasmid which contained the gene of interest and subsequently purified by affinity chromatography. A new HPLC method capable of separating the compound and product peaks with good resolution was optimized and applied to the analysis of the compounds. Results obtained show that cyclic di-inosinylic acid 1b demonstrates a stronger inhibition on Slr1143 than c-di-GMP and is a potential inhibitor for biofilm formation. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.068
• 作为产物：
  描述：

  在 triethylamine tris(hydrogen fluoride) 作用下， 反应 12.0h， 生成 乙基3,4,5-三[[(6-重氮基-5,6-二氢-5-羰基-1-萘基)磺基基]氧代]苯酸酯
  参考文献：
  名称：

  Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase

  摘要：

  Five analogs of cyclic di-nucleotidic acid including c-di-GMP were synthesized and evaluated for their biological activities on Slr1143, a diguanylate cyclase of Synechocystis sp. Slr1143 was overexpressed from the recombinant plasmid which contained the gene of interest and subsequently purified by affinity chromatography. A new HPLC method capable of separating the compound and product peaks with good resolution was optimized and applied to the analysis of the compounds. Results obtained show that cyclic di-inosinylic acid 1b demonstrates a stronger inhibition on Slr1143 than c-di-GMP and is a potential inhibitor for biofilm formation. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.068

文献信息

• Cyclic Oligoribonucleotides (RNA) by Solid-Phase Synthesis
  作者：Ronald Micura

  DOI：10.1002/(sici)1521-3765(19990702)5:7<2077::aid-chem2077>3.0.co;2-u

  日期：1999.7.2

  A novel solid-phase synthesis of small- to medium-sized cyclic RNA oligonucleotides is presented. A major advantage of the approach is the lack of restrictions on the sequence variety with respect to the four standard bases adenine, cytosine, guanine, and uracil. This has been demonstrated for cycles containing 2 to 21 nucleotide units. The approach allows fully automated assembly, and is related to a procedure known for the preparation of cyclic oligonucleotides in the DNA series (E. Alazzouzi. N. Escaja, A. Grandas, E. Pedroso, Angew. Chem. 1997, 109, 1564 - 1567; Angew. Chem. Int. Ed. Engl. 1997, 36, 1506 - 1508). It combines standard phosphoramidite chemistry for chain elongation and standard phosphotriester chemistry for ring closure. A key aspect of the method is use of the novel 2'-O-triiso-propylsilyloxymethyl (TOM) protected RNA phosphoramidites (X. Wu, S. Pitsch, Nucleic Acids Res. 1998, 26, 4315 - 4323) instead of the classic tert-butyldimethyl silyl (TBDMS) protected amidites. Furthermore, the design of the final cleavage step is selective only for correctly cyclized oligoribonucleotides. This results, after deprotection, in HPLC profiles in which the crude oligonucleotide is represented by the major peak with typically more than 80 % of the integrated area. The ring closure itself proceeds with an average yield of 15 %.
• Making cyclic RNAs easily available
  作者：Miriam Frieden、Anna Grandas、Enrique Pedroso

  DOI：10.1039/a904851k

  日期：——

  A simple solid-phase procedure allows cyclic oligoribonucleotides to be obtained as long as the linear precursor attached to the support has a 2′-deoxyribonucleoside or a 2′-O-methylribonucleoside at the 3′-end.