N-isobutyryl-β-L-2'-deoxyguanosine | 141771-79-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N-isobutyryl-β-L-2'-deoxyguanosine
• 英文别名: β-L-dG^Ibu；N-[9-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 141771-79-1
• 化学式: C₁₄H₁₉N₅O₅
• 分子量: 337.335
• InChiKey: SIDXEQFMTMICKG-VGMNWLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  24
• 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：

  N-isobutyryl-β-L-2'-deoxyguanosine 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.03h， 生成 (2S,3R,5S)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(2-isobutyramido-6-oxo-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite
  参考文献：
  名称：

  Enantio- and meso-DNAs: preparation, characterization, and interaction with complementary nucleic acids

  摘要：

  Enantio-DNAs (DNA having 2-deoxy-L-erythro-pentose, the enantiomer of natural 2-deoxy-D-ribose, as the sugar backbone) and meso-DNAs (DNA having an alternating sequence of L-sugars and D-sugars) were prepared by the use of an automated DNA synthesizer. The characteristics of the products were analyzed, focusing on enantio- and meso-dodecadeoxyadenylic acids (designated as L-dA12 and LD-dA12, respectively). Both L-dA12 and LD-dA12 were resistant to the action of phosphodiesterases, though LD-dA12 was decomposed very slowly by snake venom phosphodiesterase. The affinity of these dodecamers for their complementary natural nucleic acids, poly(U) and poly(dT), was analyzed by the UV-mixing curve and melting-temperature measurement methods. Both L-dA12 and LD-dA12 showed affinity for their complementary nucleic acids. L-dA12 showed high selectivity for poly(U) over poly(dT), and a UV-mixing curve analysis suggested that the interaction mode was triplex formation. LD-dA12 showed moderate selectivity for poly(U) over poly(dT). L-dT12, the counterpart of L-dA12, did not show any detectable interaction with its complementary natural nucleic acid.

  DOI：

  10.1021/ja00075a002
• 作为产物：
  描述：

  2'-deoxyguanosine 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-isobutyryl-β-L-2'-deoxyguanosine
  参考文献：
  名称：

  Enantio- and meso-DNAs: preparation, characterization, and interaction with complementary nucleic acids

  摘要：

  Enantio-DNAs (DNA having 2-deoxy-L-erythro-pentose, the enantiomer of natural 2-deoxy-D-ribose, as the sugar backbone) and meso-DNAs (DNA having an alternating sequence of L-sugars and D-sugars) were prepared by the use of an automated DNA synthesizer. The characteristics of the products were analyzed, focusing on enantio- and meso-dodecadeoxyadenylic acids (designated as L-dA12 and LD-dA12, respectively). Both L-dA12 and LD-dA12 were resistant to the action of phosphodiesterases, though LD-dA12 was decomposed very slowly by snake venom phosphodiesterase. The affinity of these dodecamers for their complementary natural nucleic acids, poly(U) and poly(dT), was analyzed by the UV-mixing curve and melting-temperature measurement methods. Both L-dA12 and LD-dA12 showed affinity for their complementary nucleic acids. L-dA12 showed high selectivity for poly(U) over poly(dT), and a UV-mixing curve analysis suggested that the interaction mode was triplex formation. LD-dA12 showed moderate selectivity for poly(U) over poly(dT). L-dT12, the counterpart of L-dA12, did not show any detectable interaction with its complementary natural nucleic acid.

  DOI：

  10.1021/ja00075a002

文献信息

• Enzymatic Parallel Kinetic Resolution of Mixtures of <scp>d</scp>/<scp>l</scp> 2′-Deoxy and Ribonucleosides: An Approach for the Isolation of β-<scp>l</scp>-Nucleosides
  作者：Saúl Martínez-Montero、Susana Fernández、Yogesh S. Sanghvi、Vicente Gotor、Miguel Ferrero

  DOI：10.1021/jo101368z

  日期：2010.10.1

  We have developed a lipase-catalyzed parallel kinetic resolution of mixtures of beta-D/L-nucleosides. The opposite selectivity during acylation exhibited by Pseudomonas cepacia lipase (PSL-C) with beta-D- and beta-L-nucleosides furnished acylated compounds that have different R-f values. As a consequence, isolation of both products was achieved by simple column chromatography. Computer modeling of the transition-state analogues during acylation of beta-D- and beta-L-2'-deoxycytidine with PSL-C was carried out to explain the high selectivity. PSL-C favored the 3'-O-levulination of the beta-D enantiomer, whereas the 5'-OH group was acylated in 2'-deoxy-beta-L-cytidine. In both cases, the cytosine base was placed in the alternate hydrophobic pocket of PSL's substrate-binding site, where it can form extra hydrogen bonds (in addition to the five essential catalytically relevant hydrogen bonds) that stabilize these intermediates catalyzing the selective acylation of beta-D/L-nucleosides.
• Regioselective Enzymatic Acylation of β-<scp>l</scp>-2‘-Deoxynucleosides:  Application in Resolution of β-<scp>d</scp>/<scp>l</scp>-2‘-Deoxynucleosides
  作者：Javier García、Susana Fernández、Miguel Ferrero、Yogesh S. Sanghvi、Vicente Gotor

  DOI：10.1021/ol048502v

  日期：2004.10.1

  (GRAPHICS)A practical synthesis Of beta-L-3'- and beta-L-5'-O-levulinyl-2'-deoxynucleosides has been described for the first time through enzymatic acylation and/or hydrolysis processes. It is noteworthy that the different behavior exhibited by Pseudomonas cepacia lipase in the acylation of D- and L-nucleosides allows the parallel kinetic resolution Of D/L-nucleosides.
• [EN] METHOD OF SEQUENCING L-POLYNUCLEOTIDE<br/>[FR] PROCÉDÉ DE SÉQUENÇAGE DE L-POLYNUCLÉOTIDE
  申请人：[en]DXOME INC.

  公开号：WO2023183345A2

  公开（公告）日：2023-09-28

  The present disclosure provides a novel method of amplifying and sequencing L-form polynucleotide. Further provided include L-form nucleotides and D-form enzymes that can be used in the method. The method of making the L-form nucleotides and D-form enzymes are also provided.
• Enantio- and meso-DNAs: preparation, characterization, and interaction with complementary nucleic acids
  作者：Yuichi Hashimoto、Naoko Iwanami、Shizuyoshi Fujimori、Koichi Shudo

  DOI：10.1021/ja00075a002

  日期：1993.11

  Enantio-DNAs (DNA having 2-deoxy-L-erythro-pentose, the enantiomer of natural 2-deoxy-D-ribose, as the sugar backbone) and meso-DNAs (DNA having an alternating sequence of L-sugars and D-sugars) were prepared by the use of an automated DNA synthesizer. The characteristics of the products were analyzed, focusing on enantio- and meso-dodecadeoxyadenylic acids (designated as L-dA12 and LD-dA12, respectively). Both L-dA12 and LD-dA12 were resistant to the action of phosphodiesterases, though LD-dA12 was decomposed very slowly by snake venom phosphodiesterase. The affinity of these dodecamers for their complementary natural nucleic acids, poly(U) and poly(dT), was analyzed by the UV-mixing curve and melting-temperature measurement methods. Both L-dA12 and LD-dA12 showed affinity for their complementary nucleic acids. L-dA12 showed high selectivity for poly(U) over poly(dT), and a UV-mixing curve analysis suggested that the interaction mode was triplex formation. LD-dA12 showed moderate selectivity for poly(U) over poly(dT). L-dT12, the counterpart of L-dA12, did not show any detectable interaction with its complementary natural nucleic acid.