{S-[1-(ω-carbonylmethyl)uracil-6-methyl]-L-cysteine methyl ester}-S-{1-[(tert-butoxy)carbonylmethyl]uracil-6-methyl}-L-cysteine methyl ester | 1275513-64-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {S-[1-(ω-carbonylmethyl)uracil-6-methyl]-L-cysteine methyl ester}-S-{1-[(tert-butoxy)carbonylmethyl]uracil-6-methyl}-L-cysteine methyl ester
• CAS: 1275513-64-8
• 化学式: C₂₆H₃₆N₆O₁₁S₂
• 分子量: 672.737
• InChiKey: BVIANNMQIWFFEB-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.95
• 重原子数：
  45.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  243.74
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  {S-[1-(ω-carbonylmethyl)uracil-6-methyl]-L-cysteine methyl ester}-S-{1-[(tert-butoxy)carbonylmethyl]uracil-6-methyl}-L-cysteine methyl ester 、 {S-[N4-(benzyloxycarbonyl)-1-(ω-carbonylmethyl)cytosine-6-methyl]-N-Fmoc-L-cysteine methyl ester}-S-{N4-(benzyloxycarbonyl)-1-(carboxymethyl)cytosine-6-methyl}-L-cysteine methyl ester 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以72%的产率得到{S-[N4-(benzyloxycarbonyl)-1-(ω-carbonylmethyl)cytosine-6-methyl]-N-Fmoc-L-cysteine Ester}-{S-[N4-(benzyloxycarbonyl)-1-(ω-carbonylmethyl)cytosine-6-methyl]-L-cysteine methyl ester}-{S-[1-(ω-carbonylmethyl)uracil-6-methyl]-L-cysteine methyl ester}-S-{1-[(tert-butoxy) carbonylmethyl]uracil-6-methyl}-L-cysteine methyl ester
  参考文献：
  名称：

  Autonomously Pairing Cysteinyl-Linked Nucleotide Analogues with a Unique Architecture

  摘要：

  We report the efficient pairing in water of the first representative of oligonucleotide analogues in which the backbone is replaced by linking elements between the nucleobases. The architecture of the new analogue demonstrates that the structural differentiation of oligonucleotides into a contiguous backbone and nucleobases, as embodied by the natural nucleic acids and all nucleotide analogues analyzed to date, is not a prerequisite for pairing. UV and circular dichroisrn analyses of self-complementary and non-self-complementary octanucleotide analogues strongly suggest the fully reversible, sequence-specific association of our new analogues to form a left-handed double helix with an antiparallel strand orientation that is characterized by melting temperatures and free enthalpies higher than those of natural RNA and DNA of the same sequence. The linking element incorporates an L-cysteine moiety that allows a short and efficient synthesis of the monomeric building blocks and, through the choice of either L- or D-cysteine, gives access to either one of the enantiomeric oligomers and thus to left- or right-handed helices.

  DOI：

  10.1021/ja200829s
• 作为产物：
  描述：

  tert-butyl 6-(chloromethyl)uracil-1-acetate 在 哌啶 、 三乙基硅烷 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 {S-[1-(ω-carbonylmethyl)uracil-6-methyl]-L-cysteine methyl ester}-S-{1-[(tert-butoxy)carbonylmethyl]uracil-6-methyl}-L-cysteine methyl ester
  参考文献：
  名称：

  Autonomously Pairing Cysteinyl-Linked Nucleotide Analogues with a Unique Architecture

  摘要：

  We report the efficient pairing in water of the first representative of oligonucleotide analogues in which the backbone is replaced by linking elements between the nucleobases. The architecture of the new analogue demonstrates that the structural differentiation of oligonucleotides into a contiguous backbone and nucleobases, as embodied by the natural nucleic acids and all nucleotide analogues analyzed to date, is not a prerequisite for pairing. UV and circular dichroisrn analyses of self-complementary and non-self-complementary octanucleotide analogues strongly suggest the fully reversible, sequence-specific association of our new analogues to form a left-handed double helix with an antiparallel strand orientation that is characterized by melting temperatures and free enthalpies higher than those of natural RNA and DNA of the same sequence. The linking element incorporates an L-cysteine moiety that allows a short and efficient synthesis of the monomeric building blocks and, through the choice of either L- or D-cysteine, gives access to either one of the enantiomeric oligomers and thus to left- or right-handed helices.

  DOI：

  10.1021/ja200829s