1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-iodo-6-[(2-methylpropanoyl)amino]-4H-pyrazolo[3,4-d]pyrimidin-4-one | 215178-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-iodo-6-[(2-methylpropanoyl)amino]-4H-pyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: N-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-iodo-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl]-2-methylpropanamide
• CAS: 215178-27-1
• 化学式: C₁₄H₁₈IN₅O₅
• 分子量: 463.232
• InChiKey: WOXDVPOWZXQYLP-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-iodo-6-[(2-methylpropanoyl)amino]-4H-pyrazolo[3,4-d]pyrimidin-4-one 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 6.0h， 生成 1-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,5-dihydro-6-[(2-methylpropanoyl)amino]-3-(3-trifluoroacetamidoprop-yl)-4H-pyrazolo[3,4-d]-pyrimidin-4-one 3-(2-cyanoethyl-diisopropylphosphoramidite)
  参考文献：
  名称：

  8–17 DNAzyme modified with purine analogs in its catalytic core: The conservation of the five-membered moieties of purine residues

  摘要：

  8-17 DNAzyme is characterized by its recurrence in different in vitro selections and versatile cleavage sites, leading to extensive studies on its structural properties and applications. We evaluated the purine residues (A6, G7, G11, A12, G14, and A15) in the catalytic core of 8-17 DNAzyme of their five-membered ring moiety with purine analogs 1-5 to have an insight into the conservation of the residues at the level of functional groups. The 7-nitrogen atom in the AGC loop was demonstrated to be strictly conserved for the cleavage reaction. But such modifications exerted favorable effect at G11 of the base-pair stem and A12 in the single-strand loop, directing toward more efficient DNAzymes. Even the most conserved G14 could tolerate such modifications. These results demonstrated that chemical modification on the functional groups is a feasible approach to gain an insight into the structural requirement in the catalytic reaction of DNAzymes. It also provided modification sites for introduction of signaling molecules used for mechanistic and folding studies of 8-17 DNAzyme. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.044
• 作为产物：
  描述：

  异丁酸酐 、 6-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-iodo-4H-pyrazolo[3,4-d]pyrimidin-4-one 在 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以66%的产率得到1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-3-iodo-6-[(2-methylpropanoyl)amino]-4H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Stabilisation of duplex DNA by 7-halogenated 8-aza-7-deazaguanines

  摘要：

  含有 7 卤化 8-aza-7-deaza-2′-deoxyguanosine (c7z8Gd) 衍生物的寡核苷酸，如 d(Br7c7z8 G-C)4 8（Tm = 88 ℃）和 d(I7c7z8 G-C)4 9（Tm = 84 ℃），比 d(G-C)4 5（Tm = 59 ℃）稳定得多。

  DOI：

  10.1039/a804414g

文献信息

• Oligonucleotides Containing Pyrazolo[3,4-d]pyrimidines: The Influence of 7-Substituted 8-Aza-7-deaza-2′-deoxyguanosines on the Duplex Structure and Stability
  作者：Frank Seela、Georg Becher

  DOI：10.1002/(sici)1522-2675(19991006)82:10<1640::aid-hlca1640>3.0.co;2-n

  日期：1999.10.6

  Oligonucleotides containing 7-substituted 8-aza-7-deazaguanines (= 6-amino-1,5-dihydro-4H-pyrazolo[3.4-d]pyrimidin-4-ones) were prepared by automated solid-phase synthesis. A series of 7-alkynylated 8-aza-7-deaza-2'-deoxyguanosines (see 4a-d)were synthesized with the 7-iodonucleoside 3c as starting material and by the Pd-0/Cu-I-catalyzed cross-coupling reaction with various alkynes. Phosphoramidites were prepared from the 7-substituted 8-aza-7-deaza-2'-deoxyguanosine derivatives carrying halogeno, cyano, and hexynyl substituents. From the melting profiles of oligonucleotide duplexes. the T-m values as well as the thermodynamic data were determined. A significant duplex stabilization by the 7-substituents was observed for the DNA . DNA duplexes, but not in the case of DNA . RNA hybrids.
• [EN] MINOR GROOVE BINDER-ENERGY TRANSFER OLIGONUCLEOTIDES AND METHODS FOR THEIR USE<br/>[FR] LIGAND DU PETIT SILLON-OLIGONUCLÉOTIDES DESTINÉS AU TRANSFERT D'ÉNERGIE ET PROCÉDÉS POUR LEUR UTILISATION
  申请人：EPOCH BIOSCIENCES INC

  公开号：WO2009058852A2

  公开（公告）日：2009-05-07

  The incorporation of a minor groove binder spaced close to one member of a matched FRET set in a minor groove binder-oligonucleotide conjugate significantly reduces background fluorescence of a FRET probe or pair of probes and, consequently, increases the S/B ratios. Fluorescent-labeled probes are useful in carrying out hybridization, multiplex nucleic acid detection, and other procedures.