5'-O-(4,4'-dimethoxytrityl)-L-thymidine | 131607-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)-L-thymidine
• 英文别名: 1-((2S,4R,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione；DMT(-5)2-deoxy-L-eryPenf(b)-thymin-1-yl；1-[(2S,4R,5S)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 131607-27-7
• 化学式: C₃₁H₃₂N₂O₇
• 分子量: 544.604
• InChiKey: UBTJZUKVKGZHAD-PKTNWEFCSA-N

物化性质

• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-L-thymidine 在 lithium hydroxide monohydrate 、 水 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.67h， 生成 1-((2S,4S,5S)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  [EN] MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS OLIGOMÈRES MODIFIÉS ET LEURS UTILISATIONS

  摘要：

  本公开提供了包含至少一种立体非标准核苷酸的修饰寡核苷酸的寡聚化合物。包括由12-30个连接的核苷酸组成的修饰寡核苷酸的寡聚化合物，其中修饰寡核苷酸的至少一个核苷酸是立体非标准核苷酸；且所述寡聚化合物选自RNAi化合物、修饰CRISPR化合物和人工mRNA化合物。

  公开号：

  WO2021030763A1
• 作为产物：
  描述：

  L-胸苷 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 吡啶 、 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-L-thymidine
  参考文献：
  名称：

  Synthesis and Enzymatic Digestion of an RNA Nonamer in Both Enantiomeric Forms

  摘要：

  The D- and L-RNA nonamers of the sequence r(GCUUCGGC)T have been synthesised for X-ray crystallographic purposes. In vitro digestion of the unnatural optical antipode by snake venom phosphodiesterase I takes place at an approximately 1800-fold slower rate than that of the natural D-nonamer. The digestion experiments showed-to our knowledge for the first time-that L-RNA can indeed be cleaved enzymatically when phosphodiesterase I from snake venom is used-as opposed to a number of cellular ribonucleases-which sheds an interesting light on the evolution and possibly structure/function relationship of venom versus cellular degradation enzymes. The broad substrate specificity of this enzyme could be taken advantage of to study and further optimise the resistance towards biodegradation of therapeutic L-RNA aptamers. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00046-6

文献信息

• L-R_{ibonucleosides for}R_acemicRNA
  作者：E. Moyroud、O. Botta、P. Strazewski

  DOI：10.1080/15257779908041544

  日期：1999.4

  Two L-ribosyl donors were synthesised from L-xylose, then submitted to a glycosidation reaction according to Vorbruggen's conditions to furnish L-ribonucleosides in high yield.
• 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.
• MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF
  申请人：Ionis Pharmaceuticals, Inc.

  公开号：EP4013428A1

  公开（公告）日：2022-06-22
• Synthesis and Enzymatic Digestion of an RNA Nonamer in Both Enantiomeric Forms
  作者：Elisabeth Moyroud、Ewa Biala、Peter Strazewski

  DOI：10.1016/s0040-4020(00)00046-6

  日期：2000.3

  The D- and L-RNA nonamers of the sequence r(GCUUCGGC)T have been synthesised for X-ray crystallographic purposes. In vitro digestion of the unnatural optical antipode by snake venom phosphodiesterase I takes place at an approximately 1800-fold slower rate than that of the natural D-nonamer. The digestion experiments showed-to our knowledge for the first time-that L-RNA can indeed be cleaved enzymatically when phosphodiesterase I from snake venom is used-as opposed to a number of cellular ribonucleases-which sheds an interesting light on the evolution and possibly structure/function relationship of venom versus cellular degradation enzymes. The broad substrate specificity of this enzyme could be taken advantage of to study and further optimise the resistance towards biodegradation of therapeutic L-RNA aptamers. (C) 2000 Elsevier Science Ltd. All rights reserved.
• [EN] MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS OLIGOMÈRES MODIFIÉS ET LEURS UTILISATIONS
  申请人：IONIS PHARMACEUTICALS INC

  公开号：WO2021030763A1

  公开（公告）日：2021-02-18

  The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.

  本公开提供了包含至少一种立体非标准核苷酸的修饰寡核苷酸的寡聚化合物。包括由12-30个连接的核苷酸组成的修饰寡核苷酸的寡聚化合物，其中修饰寡核苷酸的至少一个核苷酸是立体非标准核苷酸；且所述寡聚化合物选自RNAi化合物、修饰CRISPR化合物和人工mRNA化合物。