L-cysteine-d1

• 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: L-cysteine-d1
• 英文别名: Deutero-l-cysteine；(2R)-2-(deuterioamino)-3-sulfanylpropanoic acid
• 化学式: C₃H₇NO₂S
• 分子量: 122.152
• InChiKey: XUJNEKJLAYXESH-YHNMSJHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-cysteine-d1 在 重水 作用下， 以 水 为溶剂， 生成 L-半胱氨酸
  参考文献：
  名称：

  A new method for obtaining isotopic fractionation data at multiple sites in rapidly exchanging systems

  摘要：

  DOI：

  10.1021/ja00295a017
• 作为产物：
  描述：

  L-胱氨酸 在 硼氘化钠 、 氘氧化钠 作用下， 以 重水 为溶剂， 反应 18.0h， 生成 L-cysteine-d1
  参考文献：
  名称：

  Measuring the Aromatic Potential of Vitis vinifera L. Cv. Sauvignon Blanc Grapes by Assaying S-Cysteine Conjugates, Precursors of the Volatile Thiols Responsible for Their Varietal Aroma

  摘要：

  The method presented for measuring the aromatic potential of Sauvignon blanc must is based on an assay of the S-cysteine conjugate precursors of three volatile thiols involved in the characteristic aroma of wines made from this grape variety: 4-mercapto-4-methylpentan-2-one, 4-mercapto-4-methylpentan-2-ol, and 3-mercaptohexan-1-ol. These compounds were released enzymatically from their precursors by percolating the must through an immobilized tryptophanase column (EC 4.1.99.1), catalyzing an alpha, beta-elimination reaction on the S-cysteine conjugate. The volatile thiols were analyzed by GC-MS, as were the deuterated analogues that had been released from synthesized deuterated precursors and were added as internal standards. The quantities of volatile thiols released under these conditions were proportional to the S-cysteine conjugate content of the must.

  DOI：

  10.1021/jf990979b

文献信息

• Are Carboxyl Groups the Most Acidic Sites in Amino Acids? Gas-Phase Acidity, H/D Exchange Experiments, and Computations on Cysteine and Its Conjugate Base
  作者：Zhixin Tian、Anna Pawlow、John C. Poutsma、Steven R. Kass

  DOI：10.1021/ja0666194

  日期：2007.5.1

  Hydrogen-deuterium exchange experiments were carried out on the conjugate base of cysteine with four different deuterated alcohols. Three H/D exchanges are observed to take place in each case, and a relay mechanism which requires the SH and CO2H groups to have similar acidities and subsequently proceeds through a zwitterionic intermediate is proposed. Gas-phase acidity measurements also were carried

  在半胱氨酸与四种不同的氘化醇的共轭碱上进行氢-氘交换实验。在每种情况下都观察到三个 H/D 交换，并提出了一种中继机制，该机制需要 SH 和 CO2H 基团具有相似的酸度，然后通过两性离子中间体进行。还使用扩展动力学方法在四极离子阱中和通过平衡测定在傅立叶变换质谱仪中进行气相酸度测量。结果与高水平的从头算和密度泛函理论计算结果非常吻合，表明半胱氨酸中的侧链硫醇比羧基酸性强 3.1 kcal mol-1。因此预测去质子化的半胱氨酸是硫醇盐离子。