S-(methylseleno)cysteine | 724706-42-7

• 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-(methylseleno)cysteine
• 英文别名: S-(methylselanyl)-L-cysteine；(2R)-2-amino-3-methylselanylsulfanylpropanoic acid
• CAS: 724706-42-7
• 化学式: C₄H₉NO₂SSe
• 分子量: 214.147
• InChiKey: ZDHAKDUTQCFEKA-VKHMYHEASA-N

物化性质

• 沸点：
  347.2±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  焦碳酸二乙酯 、 S-(methylseleno)cysteine 以 吡啶 、 乙醇 、 水 为溶剂， 以47%的产率得到S-(methylseleno)cysteine ethyl ester N-ethylcarbamate
  参考文献：
  名称：

  Identification and Synthesis of a Novel Selenium−Sulfur Amino Acid Found in Selenized Yeast:  Rapid Indirect Detection NMR Methods for Characterizing Low-Level Organoselenium Compounds in Complex Matrices

  摘要：

  After proteolytic digestion, aqueous extraction, and derivatization with diethyl pyrocarbonate or ethyl chloroformate, HPI-C-incluctively coupled plasma (ICP)-MS, GC-atomic emission detection (AED), and GC-MS analysis of high-selenium yeast stored at room temperature for more than 10 years showed selenomethionine as the major Se product along with substantial amounts of selenomethionine selenoxide hydrate and the previously unreported selenoamino acid having a Se-S bond, S(methylseleno)cysteine. The identity of the latter compound was confirmed by synthesis. The natural product was shown to be different from a synthetic sample of the isomeric compound Se-(methylthio)selenocysteine. Selenium-specific NMR spectroscopic methods were developed to directly analyze the aqueous extracts of the hydrolyzed selenized yeast without derivatization or separation. Selenomethionine and S-(methylseleno)cysteine were identified by Se-77-H-1 HMQC-TOCSY experiments.

  DOI：

  10.1021/jf049887z
• 作为产物：
  描述：

  L-半胱氨酸 、 methaneselenenyl bromide 在 氢氧化钾 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.25h， 以71%的产率得到S-(methylseleno)cysteine
  参考文献：
  名称：

  Identification and Synthesis of a Novel Selenium−Sulfur Amino Acid Found in Selenized Yeast:  Rapid Indirect Detection NMR Methods for Characterizing Low-Level Organoselenium Compounds in Complex Matrices

  摘要：

  After proteolytic digestion, aqueous extraction, and derivatization with diethyl pyrocarbonate or ethyl chloroformate, HPI-C-incluctively coupled plasma (ICP)-MS, GC-atomic emission detection (AED), and GC-MS analysis of high-selenium yeast stored at room temperature for more than 10 years showed selenomethionine as the major Se product along with substantial amounts of selenomethionine selenoxide hydrate and the previously unreported selenoamino acid having a Se-S bond, S(methylseleno)cysteine. The identity of the latter compound was confirmed by synthesis. The natural product was shown to be different from a synthetic sample of the isomeric compound Se-(methylthio)selenocysteine. Selenium-specific NMR spectroscopic methods were developed to directly analyze the aqueous extracts of the hydrolyzed selenized yeast without derivatization or separation. Selenomethionine and S-(methylseleno)cysteine were identified by Se-77-H-1 HMQC-TOCSY experiments.

  DOI：

  10.1021/jf049887z