5'-dCT

• 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
• 英文名称: 5'-dCT
• 英文别名: 1-[(2R,4S,5R)-5-[[[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy-hydroxyphosphinothioyl]oxymethyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₉H₂₆N₅O₁₀PS
• 分子量: 547.483
• InChiKey: WCWBUCLHFXOEDH-PCYLLWSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  238
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 5'-dCT
  参考文献：
  名称：

  Stereo-enriched phosphorothioate oligodeoxynucleotides: synthesis, biophysical and biological properties

  摘要：

  Stereo-enriched [Rp] and [Sp]-phosphorothioate oligodeoxynucleotides are synthesized using oxazaphospholidine derivatized monomers. Three different designs of phosphorothioate oligodeoxynucleotides (PS-oligos), (i) stereo-enriched all-[Rp] or all-[Sp] PS-linkages, (ii) stereo-random mixture of PS-linkages, and (iii) segments containing certain number of stereo-enriched [Rp] and [Sp] PS-linkages ([Sp-Rp-Sp] or [Rp-Sp-Rp]), have been studied. Thermal melting studies of these PS-oligos with RNA complementary strands showed that the binding affinities are in the order [Rp] > [Sp-Rp-Sp] = [Rp-Sp-Rp] > stereo-random > [Sp]. Circular dichroism (CD) studies suggest that the stereochemistry of the PS-oligo does not affect the global conformation of the duplex. The in vitro nuclease stability of these PS-oligos is in the order [Sp] > [Sp-Rp-Sp], stereo-random > [Rp]. The RNase H activation is in the order [Rp] > stereo-random > [Rp-Sp-Rp] > [Sp] > [Sp-Rp-Sp]. Studies in a cancer cell Line of PS-oligos targeted to MDM2 mRNA showed that all oligos had similar biological activity under the experimental conditions employed. Protein- and enzyme-binding studies showed insignificant stereo-dependent binding to proteins. The [Sp] and [Sp-Rp-Sp] chimeric and stereo-random PS-oligos that contained a CpG motif showed higher cell proliferation than [Rp] PS-oligo of the same sequence. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00275-8

文献信息

• 4-Cyano-2-butenyl group: A new type of protecting group in oligonucleotide synthesis via phosphoramidite approach
  作者：Vasulinga T. Ravikumar、Zacharia S. Cheruvallath、Douglas L. Cole

  DOI：10.1016/s0040-4039(96)01496-7

  日期：1996.9

  4-Cyano-2-butenyl (CB) is a new type of protecting group for the internucleotidic bonds in the synthesis of oligodeoxyribonucleotides by the phosphoramidite approach. This group is stable to acidic conditions and can be removed under mild conditions by a δ-elimination pathway using aqueous ammonium hydroxide.

  4-氰基-2-丁烯基（CB）是通过亚磷酰胺方法合成寡脱氧核糖核苷酸中核苷酸间键的新型保护基。该基团对酸性条件稳定，在温和条件下可通过使用氢氧化铵水溶液的δ消除途径除去。
• N-pent-4-enoyl nucleosides: Application in the synthesis of support-bound and free oligonucleotide analogs by the H-phosphonate approach
  作者：Radhakrishnan P. Iyer、Theresa Devlin、Ivan Habus、Nan-Hui Ho、Dong Yu、Sudhir Agrawal

  DOI：10.1016/0040-4039(96)00066-4

  日期：1996.3

  N-pent-4-enoyl nucleoside H-phosphonates are versatile building blocks for the synthesis of support-bound and free oligonucleotide analogs.

  N-戊-4-烯酰基核苷H-膦酸酯是用于合成支持物结合的和游离的寡核苷酸类似物的通用结构单元。