N-Boc-(S)-methionine ethyl ester | 76220-80-9

• 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
• 英文名称: N-Boc-(S)-methionine ethyl ester
• 英文别名: Boc-Met-OEt；ethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoate
• CAS: 76220-80-9
• 化学式: C₁₂H₂₃NO₄S
• 分子量: 277.385
• InChiKey: LPSGTFDBHIGNCN-VIFPVBQESA-N

物化性质

• 沸点：
  389.8±37.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Boc-(S)-methionine ethyl ester 生成 1-羟基-4-(甲基硫代)-2-丁基氨基甲酸叔丁酯
  参考文献：
  名称：

  TANI, KADZUXIDEH;OTSUKA, SEHJNOSUKEH

  摘要：

  DOI：
• 作为产物：
  描述：

  溴乙烷 、 Boc-L-蛋氨酸 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以86%的产率得到N-Boc-(S)-methionine ethyl ester
  参考文献：
  名称：

  Pseudo-peptides Based on Methyl Cysteine or Methionine Inspired from Mets Motifs Found in the Copper Transporter Ctr1

  摘要：

  Most proteins involved in Cu homeostasis bind to intracellular Cu(I) in stable Cu(S-Cys)(x) environments, thanks to well-conserved cysteine-rich sequences. Similarly, the Cu(I) transport protein Ctr1, responsible for copper acquisition, binds Cu(I) in Cu(S-Met)(3) environments in conserved methionine-rich MXMXXM sequences, referred as Mets motifs. Pseudo-peptides based on a nitrilotriacetic acid scaffold and functionalized with three amino acids bearing thioether side chains, either methyl cysteine in T-1 or methionine in T-2, were synthesized as mimics of the Mets sequences found in Ctr1. These two ligands were obtained with good overall yields from commercial amino acids and demonstrate efficient chelating ability for Cu(I). Only one species, the mononuclear [CuT1,2](+) complex, was evidenced by electrospray ionizationmass spectroscopy (ESI-MS) and the circular dichroism signature obtained for the most constrained CuT1 complex having the shortest side chains showed reorganization of the pseudo-peptide scaffold upon Cu(I) complexation. Considering that thioether functions are neutral sulfur donors, the stability constants measured by competition with ferrozine are quite large: log K approximate to 10.2-10.3. The CuT1,(2) complexes are significantly more stable that those formed with linear peptides, mimicking isolated Mets motifs MXMXXM of the Cu transport protein Ctr1 (log K approximate to 5-6). This may be attributed to the preorganized pseudo-peptide scaffold, which arranges the three neutral sulfur donors toward the metal center. Such moderate affinity Cu(I) chelators are interesting for applications in chelation therapy, for instance, to induce minimum disturbance of Cu homeostasis in Wilsons disease treatments.

  DOI：

  10.1021/ic502962d

文献信息

• Inhibitors of Acyl-CoA:Cholesterol O-Acyl Transferase (ACAT) as Hypocholesterolemic Agents. 8. Incorporation of Amide or Amine Functionalities into a Series of Disubstituted Ureas and Carbamates. Effects on ACAT Inhibition in vitro and Efficacy in vivo
  作者：Patrick M. O'Brien、Drago R. Sliskovic、C. John Blankley、Bruce. D Roth、Michael W. Wilson、Katherine L. Hamelehle、Brian R. Krause、Richard L. Stanfield

  DOI：10.1021/jm00038a010

  日期：1994.6

  A series of disubstituted ureas containing amide or amine groups was prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyl transferase in vitro and to lower plasma total cholesterol in a variety of cholesterol-fed rat models in vivo. The presence of polar or ionizable functionalities within this class of compounds may impart greater aqueous solubility to those compounds and

  制备了一系列含有酰胺基或胺基的双取代脲，并评估了它们在体外抑制酰基-CoA：胆固醇O-酰基转移酶的能力以及在体内各种由胆固醇喂养的大鼠模型中降低血浆总胆固醇的能力。这类化合物中极性或可电离官能团的存在可以赋予这些化合物更大的水溶性，从而改善向肠道小肠细胞内酶位置的转运。即使是在水性媒介物中给药，这类化合物在慢性胆固醇喂养的高胆固醇血症大鼠模型中也能降低胆固醇。通常，在高胆固醇血症的急性大鼠模型中，含胺化合物比酰胺更有效和有效。进一步的结构活性关系研究表明，酰胺/胺基团的优选位置是尿素部分的β，而不是α，并且在该系列中，要获得良好的体外效果，必须存在仲胺（或酰胺）质子效力。这些化合物之一9n（-）在水性介质中给药给预先建立的高胆固醇血症的大鼠时，可降低血浆总胆固醇（-47％）和提高高密度脂蛋白胆固醇（+ 256％）。
• Solventless Mechanosynthesis of N-Protected Amino Esters
  作者：Laure Konnert、Frédéric Lamaty、Jean Martinez、Evelina Colacino

  DOI：10.1021/jo500463y

  日期：2014.5.2

  planetary ball mill proved to be more suitable for the synthesis of amino esters from N-protected amino acids via a one-pot activation/esterification reaction in the presence of various dialkyl dicarbonates or chloroformates. The spot-to-spot reactions were straightforward, leading to the final products in reduced reaction times with improved yields and simplified work-up procedures.

  N-或C-保护的氨基酸的机械化学衍生化是在无溶剂条件下在球磨机中进行的。用于制备甲振动球磨机ñ -保护的α-和β-氨基酯从相应的起始N-通过在二-的存在下，氨基甲酰反应未掩蔽的前体叔丁基酯（BOC 2 O），氯甲酸苄酯（Z-Cl）或9-芴基甲氧基羰基氯甲酸酯（Fmoc-Cl）。事实证明，行星式球磨机更适合通过一锅法从N保护的氨基酸合成氨基酯各种二碳酸二烷基酯或氯甲酸酯存在下的活化/酯化反应。点对点反应简单明了，从而缩短了反应时间，提高了收率，简化了后处理程序，从而使最终产品成为可能。
• Synthesis of amino acid esters by papain
  作者：D. Cantacuzène、F. Pascal、C. Guerreiro

  DOI：10.1016/s0040-4020(01)81493-9

  日期：1987.1
• A simple highly efficient asymmetric synthesis. Preparation and absolute configuration of 3(S)-(tert-butoxycarbonylamino)-1(S)-methyltetrahydrothiophenium tosylate
  作者：Kazuhide Tani、Sei Otsuka、Masaru Kido、Iwao Miura

  DOI：10.1021/ja00544a055

  日期：1980.11
• TANI KAZUHIDE; OTSUKA SEI; KIDO MASARU; MIURA IWAO, J. AMER. CHEM. SOC., 1980, 102, NO 24, 7394-7396
  作者：TANI KAZUHIDE、 OTSUKA SEI、 KIDO MASARU、 MIURA IWAO

  DOI：——

  日期：——