1-(Trifluoromethylsulfonyl)but-2-yne | 1145669-91-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 1-(Trifluoromethylsulfonyl)but-2-yne
• CAS: 1145669-91-5
• 化学式: C₅H₅F₃O₂S
• 分子量: 186.155
• InChiKey: LZHZYBJFKJRBSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(Trifluoromethylsulfonyl)but-2-yne 、 S-(5'-腺苷)-L-高半胱氨酸 在 甲酸 、 溶剂黄146 作用下， 生成
  参考文献：
  名称：

  Enhanced Chemical Stability of AdoMet Analogues for Improved Methyltransferase-Directed Labeling of DNA

  摘要：

  Methyltransferases catalyze specific transfers of methyl groups from the ubiquitous cofactor S-adenosyl-L-methionine (AdoMet) to various nucleophilic positions in biopolymers like DNA, RNA, and proteins. We had previously described synthesis and application of AdoMet analogues carrying sulfonium-bound 4-substituted but-2-ynyl side chains for transfer by methyltransferases. Although useful in certain applications, these cofactor analogues exhibited short lifetimes in physiological buffers. Examination of the reaction kinetics and products showed that their fast inactivation followed a different pathway than observed for AdoMet and rather involved a pH-dependent addition of a water molecule to the side chain. This side reaction was eradicated by synthesis of a series of cofactor analogues in which the separation between an electronegative group and the triple bond was increased from one to three carbon units. The designed hex-2-ynyl moiety-based cofactor analogues with terminal amino, azide, or alkyne groups showed a markedly improved enzymatic transalkylation activity and proved well suitable for methyltransferase-directed sequence-specific labeling of DNA in vitro and in bacterial cell lysates.

  DOI：

  10.1021/cb300669x