tert-butyl N-[4-[4-[3-[1-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]pentyl]tetrazol-5-yl]sulfonylpropanoylamino]butylamino]-4-oxobutyl]carbamate | 1426822-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: tert-butyl N-[4-[4-[3-[1-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]pentyl]tetrazol-5-yl]sulfonylpropanoylamino]butylamino]-4-oxobutyl]carbamate
• CAS: 1426822-75-4
• 化学式: C₃₂H₅₆N₁₀O₈S₂
• 分子量: 772.991
• InChiKey: KOESLUOYHXAKTN-QONNDPFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  52
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  278
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[4-[4-[3-[1-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]pentyl]tetrazol-5-yl]sulfonylpropanoylamino]butylamino]-4-oxobutyl]carbamate 、 在 三氟乙酸 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以66%的产率得到
  参考文献：
  名称：

  Chemical tagging of a drug target using 5-sulfonyl tetrazole

  摘要：

  Irreversible modification is one of the most promising strategies to identify cellular receptors of bioactive small molecules. Here we report that receptor proteins can be chemically tagged using a 5-sulfonyl tetrazole probe. 5-Sulfonyl tetrazole easily accepted nucleophilic attack of thiol groups, while 5-sulfinyl tetrazole did not. These functional groups were introduced into probe molecules of a natural product. Cyclosporine A, an immunosuppressant produced by a microbe, was derivatized to possess 5-sulfonyl tetrazole and a tag group, which enabled chemical tagging of cyclophilin A, the cellular receptor of cyclosporine A. Cyclosporine A derivative possessing 5-sulfinyl tetrazole could not tag cyclophilin A. This technique will allow efficient identification of cellular receptors of bioactive small molecules. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.092
• 作为产物：
  描述：

  5-(N-叔丁氧羰基氨基)-1-戊醇 在 4-二甲氨基吡啶 、 sodium azide 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 114.34h， 生成 tert-butyl N-[4-[4-[3-[1-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]pentyl]tetrazol-5-yl]sulfonylpropanoylamino]butylamino]-4-oxobutyl]carbamate
  参考文献：
  名称：

  Chemical tagging of a drug target using 5-sulfonyl tetrazole

  摘要：

  Irreversible modification is one of the most promising strategies to identify cellular receptors of bioactive small molecules. Here we report that receptor proteins can be chemically tagged using a 5-sulfonyl tetrazole probe. 5-Sulfonyl tetrazole easily accepted nucleophilic attack of thiol groups, while 5-sulfinyl tetrazole did not. These functional groups were introduced into probe molecules of a natural product. Cyclosporine A, an immunosuppressant produced by a microbe, was derivatized to possess 5-sulfonyl tetrazole and a tag group, which enabled chemical tagging of cyclophilin A, the cellular receptor of cyclosporine A. Cyclosporine A derivative possessing 5-sulfinyl tetrazole could not tag cyclophilin A. This technique will allow efficient identification of cellular receptors of bioactive small molecules. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.092

文献信息

• Chemical tagging of a drug target using 5-sulfonyl tetrazole
  作者：Satsuki Otsuki、Shinichi Nishimura、Hisae Takabatake、Kozue Nakajima、Yasuaki Takasu、Toru Yagura、Yuki Sakai、Akira Hattori、Hideaki Kakeya

  DOI：10.1016/j.bmcl.2013.01.092

  日期：2013.3

  Irreversible modification is one of the most promising strategies to identify cellular receptors of bioactive small molecules. Here we report that receptor proteins can be chemically tagged using a 5-sulfonyl tetrazole probe. 5-Sulfonyl tetrazole easily accepted nucleophilic attack of thiol groups, while 5-sulfinyl tetrazole did not. These functional groups were introduced into probe molecules of a natural product. Cyclosporine A, an immunosuppressant produced by a microbe, was derivatized to possess 5-sulfonyl tetrazole and a tag group, which enabled chemical tagging of cyclophilin A, the cellular receptor of cyclosporine A. Cyclosporine A derivative possessing 5-sulfinyl tetrazole could not tag cyclophilin A. This technique will allow efficient identification of cellular receptors of bioactive small molecules. (C) 2013 Elsevier Ltd. All rights reserved.