3'-O-苯甲酰基-2'-脱氧-N-异丁酰基鸟苷 | 63660-23-1

• 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: 3'-O-苯甲酰基-2'-脱氧-N-异丁酰基鸟苷
• 中文别名: 3'-O-苯甲酰基-2'-脱氧-N2-异丁酰基鸟苷
• 英文名称: 3'-O-benzoyl-N²-isobutyryl-2'-deoxyguanosine
• 英文别名: 2'-deoxy-N-(2-methyl-1-oxopropyl)guanosine 3'-benzoate；2'-Deoxy-N-(2-methyl-1-oxopropyl)guanosine 3'-benzoate；[(2R,3S,5R)-2-(hydroxymethyl)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] benzoate
• CAS: 63660-23-1
• 化学式: C₂₁H₂₃N₅O₆
• mdl: MFCD00036250
• 分子量: 441.444
• InChiKey: LIOWMNSJEHKBBW-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-O-苯甲酰基-2'-脱氧-N-异丁酰基鸟苷 在 苯磺酸 、 1-(均三甲苯基磺酰基)-4-硝基-1H-咪唑 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 17.25h， 生成 Benzoic acid (2R,3S,5R)-2-[[(2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yloxy]-(4-chloro-phenoxy)-phosphoryloxymethyl]-5-(2-isobutyrylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  脱氧核糖核酸及其相关化合物的研究。三，通过改进的三酯法合成与大肠杆菌tRNAfmet的反密码子环互补的寡脱氧核糖核苷酸。

  摘要：

  p-氯苯基 N-(对甲氧苯基)氯代磷酰胺酯被用来磷酸化N,5'-O-保护的脱氧核苷的3'-羟基。这些核苷酸作为合成全保护的寡脱氧核苷酸的3'-末端单元，而对甲氧基苯胺可便利地通过用异戊基亚硝酸盐处理来除去，生成用于缩合的3'-磷酸二酯。这种方法适合通过色谱法对全保护的寡脱氧核苷酸进行完全纯化，这是获取产品的关键。通过将二、三和四核苷酸块(dATP、dTATP和dTTATP)与保护的dGAG缩合，合成了与大肠杆菌tRNAMetf反密码子环互补的脱氧寡核苷酸。产物(dA-T-G-A-G、d-T-A-T-G-A-G和d-T-T-A-T-G-A-G)通过阴离子交换或反相高效液相色谱法分离。

  DOI：

  10.1248/cpb.29.3440
• 作为产物：
  描述：

  N2-异丁酰-5'-O-(4,4'-二甲氧基三苯基)-2'-脱氧鸟苷 在 吡啶 、 苯磺酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 4.0h， 生成 3'-O-苯甲酰基-2'-脱氧-N-异丁酰基鸟苷
  参考文献：
  名称：

  Seliger, Hartmut; Bach, Trung-Chinh; Siewert, Gerhard, Liebigs Annalen der Chemie, 1984, # 5, p. 835 - 853

  摘要：

  DOI：

文献信息

• Rapid synthesis of oligodeoxynucleotides by using N-methylimidazole as a condensation catalyst. Syntheses of dodecanucleotides corresponding to complementary deoxyribonucleic acid of the tetrapeptide fragments of cholecystokinin-pancreozymin and vasoactive intestinal peptide.
  作者：TOSHIAKI WAKABAYASHI、SHINRO TACHIBANA

  DOI：10.1248/cpb.30.3951

  日期：——

  It has been found that N-methylimidazole (MeIm) activates stable condensing reagents such as 2, 4, 6-triisopropylbenzenesulfonyl-4-nitroimidazolide (TPSNI) and mesitylenesulfonyl-4-nitroimidazolide (MSNI). Fully protected trinucleotides which could serve as key intermediates were synthesized by using MeIm and TPSNI or MSNI. These trinucleotides were utilized in the syntheses of the dodecamers, dCATCCACCCCAT and dAGCCATCTGCTT, which correspond to the specific tetrapeptides of cholecystokininpancreozymin and vasoactive intestinal peptide.

  研究发现，N-甲基咪唑（MeIm）能够活化稳定的缩合剂，如2,4,6-三异丙基苯磺酰基-4-硝基咪唑化锂（TPSNI）和间三甲苯磺酰基-4-硝基咪唑化锂（MSNI）。通过使用MeIm和TPSNI或MSNI，合成了全保护的三核苷酸，这些三核苷酸可作为关键中间体。这些三核苷酸被用于合成十二聚体，dCATCCACCCCAT和dAGCCATCTGCTT，它们分别对应于胆囊收缩素-胰酶素和血管活性肠肽的特异性四肽序列。
• Nucleotides XXIX.¹Solution Synthesis of Protected Di-2′-deoxynucleoside Phosphotriesters and Thiophosphotriesters via the Phosphoramidite Approach
  作者：A. H. Beiter、W. Pfleiderer

  DOI：10.1055/s-1989-27299

  日期：——

  The synthesis of the fully protected 16 possible natural di-2′-deoxynucleoside phosphotriesters 6aa-dd and 16 thiophosphotriesters 7aa-dd was achieved by the phosphoramidite approach in solution in preparative scale. The 5′-O-dimethoxytrityl-2′-deoxyribonucleoside 3′-[2-(p-nitrophenyl)ethyl] phosphoromorpholidites 3a-d and the 3′-O-benzyl-2′-deoxyribonucleosides 4a-d were used as starting materials.

  通过溶液中的磷酸铵法，成功合成了16种完全保护的自然二-2′-脱氧核苷磷酸三酯6aa-dd和16种硫代磷酸三酯7aa-dd，达到制备规模。使用的起始材料是5′-O-二甲氧基三苯甲基-2′-脱氧核苷3′-[2-(对硝基苯基)乙基]磷酸吗啉酯3a-d和3′-O-苄基-2′-脱氧核苷4a-d。
• Synthesis of Bis(deoxyribonucleoside) Phosphoromorpholidate Derivatives for Oligodeoxyribonucleotide Preparation by Use of a Selective Phosphitylating Reagent
  作者：Hiroaki Ozaki、Shuhei Yamoto、Seiichirou Maikuma、Kenichi Honda、Takeo Shimidzu

  DOI：10.1246/bcsj.62.3869

  日期：1989.12

  5′-O-protected deoxyribonucleoside phosphorobisamidite with the second deoxyribonucleoside (coupling), and c) a nonaqueous oxidation with t-BuOOH (oxidation). In the coupling step, the 5′-O-protected deoxyribonucleoside phosphorobisamidite was selectively reacted with 5′-OH group of the second deoxyribonucleoside, and therefore, a protection of hydroxyl groups of the second deoxyribonucleoside is not necessary

  已使用吗啉二 (1-四唑基) 膦作为磷酸化试剂合成了序列定义的双 (脱氧核糖核苷) 磷酸吗啉衍生物作为制备寡脱氧核糖核苷酸的稳定中间体。一般程序由以下步骤组成（原位）；a) 5'-O-保护的脱氧核糖核苷与吗啉二(1-四唑基)膦（磷酸化）的反应，b) 所得的 5'-O-保护的脱氧核糖核苷磷二酰胺与第二个脱氧核糖核苷（偶联）的反应，和 c)用 t-BuOOH 进行非水氧化（氧化）。在偶联步骤中，5'-O-保护的脱氧核糖核苷磷二酰胺选择性地与第二脱氧核糖核苷的5'-OH基团反应，因此不需要对第二脱氧核糖核苷的羟基进行保护。
• Polymer support synthesis of oligodeoxyribonucleotide with an aminoethyl or aminohexyl group at the 5' end by the phosphite-triester approach.
  作者：TOSHIKI TANAKA、YASUKI YAMADA、MORIO IKEHARA

  DOI：10.1248/cpb.36.1386

  日期：——

  An N-monomethoxytrityloxyethyl or-hexyl group was introduced onto the 5'-phosphoryl group of N-protected-3'-benzoyldeoxynucleosides. After 3'-O-debenzoylation and phosphitylation, they were converted 3'-phosphoramidite derivatives. These were used at the last coupling reaction in the synthesis of octadecadeoxynucleotides with an aminoethyl or aminohexyl group at the 5' end by the phosphite-triester method on long-chain alkylamine controlled pore glass beads. Partially deblocked oligomers, after thiophenol and ammonia treatment, were separated rapidly on a reversed-phase C-18 silica gel column by utilizing the hydrophobic nature of the monomethoxy-trityl group. After AcOH treatment, the octadecamers with an aminoethyl or aminohyxyl group at the 5' end were obtained and then coupled with a fluorescent compound. The ultraviolet-temperature profiles were measured after hybridization with a complementary oligonucleotide.

  在N-保护的3'-苯甲氧基脱氧核糖核苷的5'-磷酸基团上引入了N-单甲氧基三苯基氧乙基或六基团。经过3'-O-去苯甲酰化和磷酰化后，它们被转化为3'-磷酰胺衍生物。这些衍生物在合成具有氨基乙基或氨基己基的18个脱氧核苷酸的最后偶联反应中使用，采用磷酸三酯法在长链烷基胺控制的孔玻璃珠上进行。经过硫酚和氨处理的部分去保护寡聚物，通过利用单甲氧基三苯基基团的疏水性，迅速在反相C-18硅胶柱上分离。经过醋酸处理，获得了5'端带有氨基乙基或氨基己基的18聚体，随后与荧光化合物进行偶联。与互补寡核苷酸杂交后，测量了紫外-温度特征。
• Chemical synthesis of deoxyribonucleotide with a 5'-phosphoryl group on a polystyrene polymer support by the phosphotriester method.
  作者：TOSHIKI TANAKA、YASUKI YAMADA、MORIO IKEHARA

  DOI：10.1248/cpb.35.2726

  日期：——

  Highly lipophilic amines [trityloxyethylamine (TEAm) and N-trityloxyethylaniline (TEAn)] were introduced onto a 5'-phosphoryl group and the stability of the phosphoramidate linkage to acid was studied at the diester level. It was found that the phosphoramidate linkage using TEAn was cleaved by 80% aqueous acetic acid within 1 h at room temperature. However, it required 2 h to remove TEAm from the phosphate. By using the TEAn group, 5'-phosphorylated pentadecadeoxyribonucleotide pTCCAGGGTCTGGTAC was synthesized on a polystyrene support by the phosphotriester method. After partial deblocking, the pentadecamer with the TEAn group could be easily isolated on a reversed-phase column due to the high lipophilicity of the TEAn group. The chemically synthesized 5 '-phosphorylated pentadecamer was successfully joined by using deoxyribonucleic acid ligase in the presence of a template.

  高度脂溶性的胺类化合物 [三苯氧乙胺 (TEAm) 和 N-三苯氧乙基苯胺 (TEAn)] 被引入到 5' - 磷酸基团上，并研究了磷酰胺链接对酸的稳定性。在二酯水平上进行的研究发现，使用 TEAn 的磷酰胺链接在室温下可以在 1 小时内被 80% 水合醋酸切断。然而，从磷酸中去除 TEAm 需时 2 小时。通过使用 TEAn 基团，在聚苯乙烯支架上采用磷三酯法合成了 5' - 磷酸化的十五核脱氧核糖核酸 pTCCAGGGTCTGGTAC。经过部分去阻断后，具有 TEAn 基团的十五聚核苷酸由于 TEAn 基团的高脂溶性，可以在反相色谱柱上轻松分离。该化学合成的 5' - 磷酸化十五聚核苷酸成功地在模板存在下通过脱氧核糖核酸连接酶连接。