2'-O-methylpseudoisocytidine | 133648-43-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2'-O-methylpseudoisocytidine
• 英文别名: 2-amino-5-[(2S,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-1H-pyrimidin-6-one
• CAS: 133648-43-8
• 化学式: C₁₀H₁₅N₃O₅
• 分子量: 257.246
• InChiKey: LZBWDWSLRGLACI-OOJXKGFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3,2'-O-trimethyl-5'-O-(dimethoxytrityl)pseudouridine 在 sodium ethanolate 、 溶剂黄146 作用下， 反应 24.83h， 生成 2'-O-methylpseudoisocytidine
  参考文献：
  名称：

  Triplex formation of an oligonucleotide containing 2'-O-methylpseudoisocytidine with a DNA duplex at neutral pH

  摘要：

  The synthesis of the hexadecanucleotide 5'TTTT1TTTT111111T3' (1-16mer) containing 2-amino-5-(2-O-methyl-beta-D-ribofuranosyl)-4(1H)-pyrimidinone (2'-O-methylpseudoisocytidine or 1) is described. Triplex formation of 1-16mer with a deoxyribonucleotide duplex 5'd(ACCAAAAGAAAAGGGGGGACCA)3'-5'd-(TGGTCCCCCCTTTTCTTTTGGT)3' (duplex-22) which contains the "polypurine tract" found in the genome of human T-cell leukaemia (lymphotropic) virus (HTLV-III) was studied by thermal denaturation and circular dichroiam (CD) spectra in aqueous solution at neutral pH. The "polypurine tract" contains a homoguanine cluster consisting of 6 deoxyguanine residues. The results indicate that 1-16mer and duplex-22 formed a triplex at neutral condition (0.01 M Na cacodylate, 0.5 M NaCl, 5 mM MgCl2, pH 7.2. T(m) = 20-degrees-C). In contrast, a hexadecadeoxynucleotide, 5'TTTTMTTTTMMMMMMT3'(M-16mer), containing 5-methyl-2-deoxycytidine (M) did not form a stable triplex with duplex-22 at the same condition (T(m) < 0-degrees-C). The CD mixing titration indicated that the triplex was formed with 1:1 (duplex:third strand) molecular stoichiometry.

  DOI：

  10.1021/jo00037a048

文献信息

• Triplex formation of oligonucleotides containing 2'-O-methylpseudoisocytidine in substitution for 2'-deoxycytidine
  作者：Akira Ono、Paul O. P. Ts'o、Lou Sing Kan

  DOI：10.1021/ja00010a077

  日期：1991.5
• Triplex formation of an oligonucleotide containing 2'-O-methylpseudoisocytidine with a DNA duplex at neutral pH
  作者：Akira Ono、Paul O. P. Ts'o、Lou Sing Kan

  DOI：10.1021/jo00037a048

  日期：1992.5

  The synthesis of the hexadecanucleotide 5'TTTT1TTTT111111T3' (1-16mer) containing 2-amino-5-(2-O-methyl-beta-D-ribofuranosyl)-4(1H)-pyrimidinone (2'-O-methylpseudoisocytidine or 1) is described. Triplex formation of 1-16mer with a deoxyribonucleotide duplex 5'd(ACCAAAAGAAAAGGGGGGACCA)3'-5'd-(TGGTCCCCCCTTTTCTTTTGGT)3' (duplex-22) which contains the "polypurine tract" found in the genome of human T-cell leukaemia (lymphotropic) virus (HTLV-III) was studied by thermal denaturation and circular dichroiam (CD) spectra in aqueous solution at neutral pH. The "polypurine tract" contains a homoguanine cluster consisting of 6 deoxyguanine residues. The results indicate that 1-16mer and duplex-22 formed a triplex at neutral condition (0.01 M Na cacodylate, 0.5 M NaCl, 5 mM MgCl2, pH 7.2. T(m) = 20-degrees-C). In contrast, a hexadecadeoxynucleotide, 5'TTTTMTTTTMMMMMMT3'(M-16mer), containing 5-methyl-2-deoxycytidine (M) did not form a stable triplex with duplex-22 at the same condition (T(m) < 0-degrees-C). The CD mixing titration indicated that the triplex was formed with 1:1 (duplex:third strand) molecular stoichiometry.