S,N,N-三甲基半胱氨酸 | 70706-62-6

• 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: S,N,N-三甲基半胱氨酸
• 英文名称: (R)-N,N-dimethyl-S-methylcysteine
• 英文别名: S-methyl-N,N-dimethyl-L-cysteine；S,N,N-trimethyl-L-cysteine；(2R)-2-(dimethylamino)-3-methylsulfanylpropanoic acid
• CAS: 70706-62-6
• 化学式: C₆H₁₃NO₂S
• 分子量: 163.241
• InChiKey: UHEVNORSIGNMLR-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  S,N,N-三甲基半胱氨酸 在 lithium aluminium tetrahydride 、 1,8-双二甲氨基萘 作用下， 以 四氢呋喃 为溶剂， 反应 6.08h， 生成
  参考文献：
  名称：

  L-Cysteine-, L-methionine- and D-penicillamine-derived ligands for transition metal catalyzed carbon-carbon bond-forming reactions

  摘要：

  DOI：

  10.1021/jo00218a004
• 作为产物：
  描述：

  聚合甲醛 、 S-甲基-L-半胱氨酸 在 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 1.08h， 生成 S,N,N-三甲基半胱氨酸
  参考文献：
  名称：

  通过还原胺化增强质谱信号

  摘要：

  摘要 在甲醛存在下进行还原胺化的有机硫化合物 (OSC) 表现出增加的质谱信号强度。在这项研究中，使用同位素甲醛生成了四种 OSC，包括 S-烯丙基半胱氨酸、S-烯丙基半胱氨酸亚砜、S-甲基半胱氨酸和 S-乙基半胱氨酸，并比较了改性和未改性 OSC 的质谱信号强度。这种比较涉及串联质谱输注和检测技术，例如选择离子监测 (SIM) 和多反应监测 (MRM)。输注修饰后的 OSCs 的信号强度从 2.6 倍增加到 39.2 倍，SIM 从 50.0 倍增加到 479.6 倍，MRM 从 146.4 倍增加到 2494.8 倍。带有伯胺基团的化合物以高收率与甲醛反应，并在氰基硼氢化钠存在下进行还原胺化，在这些胺基团上形成二甲基。修饰的 OSC 显示出增强的强度，因为给电子的二甲基基团增加了它们的碱性。这种信号增强有望提高绝对定量和结构表征中的检测限。因此，涉及伯胺基团的还原胺化可用于增强质谱信号

  DOI：

  10.1016/j.ijms.2015.06.010

文献信息

• Metal complexes of new chiral tridentate ligands with N, P and S donors: The crystal structure of [(S)-Ph2POCH2CH(NMe2)CH2CH2SCH3]W(CO)3
  作者：J.W. Faller、Naijie Zhang、Kevin J. Chase、W.Kenneth Musker、Anthony R. Amaro、Christopher M. Semko

  DOI：10.1016/0022-328x(94)80047-2

  日期：1994.4

  Two new ligands, (S)-Ph2POCH2CH(NMe2)CH2CH2SCH3, derived from L-methionine, and (R)-Ph2POCH2CH(NMe2)CH2-SCH3 from L-cysteine have been prepared and characterized. Several metal complexes of Pd, Mo and W have been prepared. These ligands produce a chiral electronically asymmetric environment at the metal that is evidenced by trans influences on the other ligands. A crystal structure has been determined

  两个新的配体，（小号）-Ph 2 POCH 2 CH（NME 2）CH 2 CH 2 SCH 3，衍生自大号-甲硫氨酸，和（- [R）-Ph 2 POCH 2 CH（NME 2）CH 2 -SCH 3从已经制备并表征了L-半胱氨酸。已经制备了Pd，Mo和W的几种金属配合物。这些配体在金属上产生手性电子不对称环境，这可以通过反式影响其他配体来证明。已确定[（S）-Ph 2的晶体结构POCH 2 CH（NMe 2）CH 2 CH 2 SCH 3 ] W（CO）3。硫在固体中采用S s构型，并且在羰基的度量参数中观察到明显的反式影响。这个钨单斜空间群复杂结晶P 2 1与一个= 8.8435（6），b = 14.384（1）埃，c ^ = 9.546（1）埃，β = 107.01（8），Ž = 2和V = 1161.0（4）3。
• Cysteine based novel noncompetitive inhibitors of urease(s)—Distinctive inhibition susceptibility of microbial and plant ureases
  作者：Zareen Amtul、Naheed Kausar、Cristian Follmer、Richard F. Rozmahel、Atta-Ur-Rahman、Syed Arif Kazmi、Mohammed Saleh Shekhani、Jason L. Eriksen、Khalid M. Khan、Mohammad Iqbal Choudhary

  DOI：10.1016/j.bmc.2006.05.078

  日期：2006.10

  Based on the catalysis mechanism of urease, a homologous series of 10 cysteine derivatives (CysDs) was designed and synthesized, and their inhibitory activities were evaluated for microbial ureases (Bacillus pasteurii, BPU, and Proteus mirabilis, PMU) and for a plant urease [jack bean (Cavavalia ensiformis), JBU]. As already described, thiol-compounds might inhibit urease activity by chelating the nickel atoms involved in the catalysis process. In contrast to cysteine, which has been reported to be a very weak urease inhibitor, we verified a potential inhibitory activity of these CysDs. The kinetic data demonstrate that thiol derivatives are more effective than the respective thioether derivatives. Besides, thiol-CysDs had a reduced activity in acidic pH (5.0). Lineweaver-Burk plots indicated that the nature of inhibition was of noncompetitive type for all 10 compounds, with the minimum K-i value of 2 mu M for N,N-dimethyl L-cysteine. It is proposed that these classes of compounds are more potent inhibitors of the bacterial ureases, compared with the plant-originated urease. Since microbial urease is directly involved in the infection process of many pathological organisms, this work demonstrates that thiol-CysDs represent a class of new potential urease inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.
• L-Cysteine-, L-methionine- and D-penicillamine-derived ligands for transition metal catalyzed carbon-carbon bond-forming reactions
  作者：John H. Griffin、Richard M. Kellogg

  DOI：10.1021/jo00218a004

  日期：1985.9
• Mass spectrometry signal enhancement by reductive amination
  作者：Meng-Chieh Liu、Yi-Reng Lin、Mei-Fang Huang、De-Cheng Tsai、Shih-Shin Liang

  DOI：10.1016/j.ijms.2015.06.010

  日期：2015.8

  Abstract Organosulfur compounds (OSCs) subjected to reductive amination in the presence of formaldehyde exhibited increased mass spectrometry signal intensities. In this study, four OSCs including S -allyl cysteine, S -allylcysteinine sulfoxide, S -methylcysteine and S -ethylcysteine were generated using isotopic formaldehyde, and mass spectrometry signal intensities of modified and unmodified OSCs

  摘要 在甲醛存在下进行还原胺化的有机硫化合物 (OSC) 表现出增加的质谱信号强度。在这项研究中，使用同位素甲醛生成了四种 OSC，包括 S-烯丙基半胱氨酸、S-烯丙基半胱氨酸亚砜、S-甲基半胱氨酸和 S-乙基半胱氨酸，并比较了改性和未改性 OSC 的质谱信号强度。这种比较涉及串联质谱输注和检测技术，例如选择离子监测 (SIM) 和多反应监测 (MRM)。输注修饰后的 OSCs 的信号强度从 2.6 倍增加到 39.2 倍，SIM 从 50.0 倍增加到 479.6 倍，MRM 从 146.4 倍增加到 2494.8 倍。带有伯胺基团的化合物以高收率与甲醛反应，并在氰基硼氢化钠存在下进行还原胺化，在这些胺基团上形成二甲基。修饰的 OSC 显示出增强的强度，因为给电子的二甲基基团增加了它们的碱性。这种信号增强有望提高绝对定量和结构表征中的检测限。因此，涉及伯胺基团的还原胺化可用于增强质谱信号