N-乙酰基-S-(3-丁烯基)-L-半胱氨酸甲酯 | 1043521-58-9

• 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
• 中文名称: N-乙酰基-S-(3-丁烯基)-L-半胱氨酸甲酯
• 英文名称: N-acetyl-S-(3-butenyl)-L-cysteine methyl ester
• 英文别名: methyl N-acetyl-S-(3-butenyl)-L-cysteinate；methyl (2R)-2-acetamido-3-but-3-enylsulfanylpropanoate
• CAS: 1043521-58-9
• 化学式: C₁₀H₁₇NO₃S
• 分子量: 231.316
• InChiKey: XPGUCFNFNFBXJM-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-乙酰基-S-(3-丁烯基)-L-半胱氨酸甲酯 在 ammonium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 以97%的产率得到N-acetyl-S-(3-butenyl)-L-cysteine amide
  参考文献：
  名称：

  Allyl Sulfides Are Privileged Substrates in Aqueous Cross-Metathesis: Application to Site-Selective Protein Modification

  摘要：

  Allyl sulfides undergo efficient cross-metathesis in aqueous media with Hoveyda-Grubbs second generation catalyst 1. The high reactivity of allyl sulfides in cross-metathesis was exploited in the first examples of cross-metathesis on a protein surface. S-Allylcysteine was incorporated chemically into the protein, providing the requisite allyl sulfide handle. Preliminary efforts to genetically incorporate S-allylcysteine into proteins are also reported.

  DOI：

  10.1021/ja8026168
• 作为产物：
  描述：

  4-溴-1-丁烯 、 N-乙酰基-L-半胱氨酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到N-乙酰基-S-(3-丁烯基)-L-半胱氨酸甲酯
  参考文献：
  名称：

  Allyl Sulfides Are Privileged Substrates in Aqueous Cross-Metathesis: Application to Site-Selective Protein Modification

  摘要：

  Allyl sulfides undergo efficient cross-metathesis in aqueous media with Hoveyda-Grubbs second generation catalyst 1. The high reactivity of allyl sulfides in cross-metathesis was exploited in the first examples of cross-metathesis on a protein surface. S-Allylcysteine was incorporated chemically into the protein, providing the requisite allyl sulfide handle. Preliminary efforts to genetically incorporate S-allylcysteine into proteins are also reported.

  DOI：

  10.1021/ja8026168

文献信息

• Stereoselective Synthesis of the Urinary Metabolite <i>N</i>-Acetyl-<i>S</i>-(3,4-dihydroxybutyl)cysteine
  作者：Kamlesh Sharma、J. B. Laurens、Lynne A. Pilcher

  DOI：10.1080/00397910802527763

  日期：2009.3.25

  On exposure to the potential carcinogen 1,3-butadiene, the major urinary metabolite in humans is N-acetyl-S-(3,4-dihydroxybutyl)cysteine. A novel, stereoselective synthesis of this cysteine-butadiene metabolite has been developed that is suitable for the production of either diastereomer for use in occupational exposure analysis. L-Cysteine and 4-bromo-1-butene are coupled via an SN2 reaction to give the core structure. A Sharpless asymmetric dihydroxylation using the dihydroquinidine (DHQD) ligand provided the terminal 1,2-diol with the 3-hydroxyl group in the R configuration. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental resource.
• Allyl Sulfides Are Privileged Substrates in Aqueous Cross-Metathesis: Application to Site-Selective Protein Modification
  作者：Yuya A. Lin、Justin M. Chalker、Nicola Floyd、Gonçalo J. L. Bernardes、Benjamin G. Davis

  DOI：10.1021/ja8026168

  日期：2008.7.1

  Allyl sulfides undergo efficient cross-metathesis in aqueous media with Hoveyda-Grubbs second generation catalyst 1. The high reactivity of allyl sulfides in cross-metathesis was exploited in the first examples of cross-metathesis on a protein surface. S-Allylcysteine was incorporated chemically into the protein, providing the requisite allyl sulfide handle. Preliminary efforts to genetically incorporate S-allylcysteine into proteins are also reported.