DL-methionine methyl ester | 10332-17-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: DL-methionine methyl ester
• 英文别名: methionine methyl ester；methyl 2-amino-4-methylsulfanylbutanoate
• CAS: 10332-17-9
• 化学式: C₆H₁₃NO₂S
• mdl: MFCD03940111
• 分子量: 163.241
• InChiKey: UIHPNZDZCOEZEN-UHFFFAOYSA-N

物化性质

• 熔点：
  147-150 °C
• 沸点：
  121-123 °C(Press: 12 Torr)
• 密度：
  1.1001 g/cm3(Temp: 22.5 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  DL-methionine methyl ester 在 sodium hydroxide 、 3-chlorocamphor-8-sulfonic acid 作用下， 生成 L-蛋氨酸
  参考文献：
  名称：

  Tatsuoka et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 1277

  摘要：

  DOI：
• 作为产物：
  描述：

  DL-蛋氨酸 生成 DL-methionine methyl ester
  参考文献：
  名称：

  BUYUKTIMKIN, NADIR;BUSCHAUER, ARMIN, J. CHROMATOGR., 450,(1988) N 2, C. 281-283

  摘要：

  DOI：
• 作为试剂：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 N-羟基丁二酰亚胺 、 DL-methionine methyl ester 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.25h， 生成 (S)-2-((1R,2S,6R,7S)-3,5-Dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl)-4-methylsulfanyl-butyric acid methyl ester
  参考文献：
  名称：

  Demonstration of endo-cis-(2S,3R)-Bicyclo[2.2.1]hept-5-en-2,3- dicarbonyl Unit as a Reverse-Turn Scaffold and Nucleator of Two-Stranded Parallel β-Sheets:  Design, Synthesis, Crystal Structure, and Self-Assembling Properties of Norborneno Peptide Analogues

  摘要：

  endo-cis-(2S,3R)-Bicyclo[2.2.1]hept-5-en (norbornene) dicarbonyl unit with a built-in U-architecture has been demonstrated to be an excellent reverse-turn molecular scaffold. A large variety of endo-cis-(2S,3R)-norborneno bispeptides containing almost all of the coded amino acids were synthesized and examined for conformational preferences by H-1 NMR, FT-IR, CD, and X-ray crystallographic studies. While FT-IR and H-1 NMR variable-temperature studies ruled out the presence of any significant amount of intramolecular hydrogen bonding in simple bispeptides (3a-h) (except in Aib bispeptide), the CD studies were clearly in favor of a beta-turn type structure. Single-crystal X-ray studies on Aib, Val and Leu containing norborneno bispeptides (3b-d) provided convincing proof for the presence of reverse-turn conformation. While the interstrand C-alpha-C-alpha' distances (5.2-5.7 Angstrom) were well within the range of those for beta-turn structures, no interstrand intramolecular hydrogen bonding was seen in Val and Leu bispeptides; the Aib bispeptide forms a seven-membered hydrogen-bonded ring, thus, showing that the norbornene (2S,3R)-dicarbonyl template assembles peptide chains in reverse-turn conformation by virtue of its built-in U-shaped architecture at these positions, and hydrogen bonding may not be necessary to stabilize the turn structure. The endo-cis-(2S,3R) orientation of bispeptide chains is essential for turn structure as shown by the crystal structure of trans-(2R, 3R) and trans-(2S,3S) derivative of Val bispeptide wherein the two peptide chains move away from each other with the C-alpha-C-alpha' distance increasing to 7.1-8.2 Angstrom. The norbornene 5,6-double bond was hydrogenated to 5,6-dihydro derivative which showed almost the same CD spectrum as its olefinic analogue. Oxidative cleavage [Ru (VIII)] of the 5,6-double bond in norborneno bispeptides, as demonstrated with Leu bispeptide, afforded novel cyclopentanoid peptide analogues. The promise of norbornene unit as a template for nucleating the formation of two-stranded parallel beta-sheets with minimum structural complexity is shown by the preparation of higher members of norborneno bispeptides with the general structure NBE(Pep)(2) [NBE = endo-cis-(2S,3R)-bicyclo[2.2.1]hept-5-en (norbornene) dicarbonyl unit; Pep = peptide strand with two, three, or four (same or different) amino acid residues]. In H-1 NMR, the high (3)J(HN alpha) values (7.0-9.3 Hz) observed for the amide protons (Table 5) coupled with the presence of medium to strong intrastrand sequential ROE connectivities d(alpha N(i,i+1)) spanning the entire three- or four-residue sequence in the peptide strands of 9a-e and 10 and the exhibition of relatively low-temperature coefficients (d delta/dT = -0.2 to -3.4 ppb/K) for amide protons in DMSO-d(6) solvent (Table 4) clearly suggested that hydrogen-bonded beta-sheet conformers dominate the population. FT-IR and CD studies provided further support for parallel beta-sheet structures. A particularly unique feature of the norborneno bispeptides is their strong tendency to self-assemble in the solid state.Thus, while endo-cis-(2S,3R)-Aib bispeptide (3b) forms 16-membered hydrogen bonded centrosymmetric dimers, the half-ester half-acid and the dicarboxylic acid derivatives of 3b self-assemble to form highly ordered hydrogen-bonded molecular ribbons. The Val and Leu cis-(2S, 3R)-bispeptides organize into hydrogen-bonded chains and the trans isomer of Val bispeptide self-assembles into hydrogen-bonded beta-sheet ribbon.

  DOI：

  10.1021/ja980143+

文献信息

• ANTIBIOTIC OLIGOPEPTIDES
  申请人：BIOXINESS PHARMACEUTICALS, INC.

  公开号：US20180298053A1

  公开（公告）日：2018-10-18

  Disclosed are methionine mimetics that possess antibiotic properties in prokaryotic cells. These mimetics are coupled to one or more optionally substituted amino acids provided that at least one of the amino acids is phenylglycine, tryptophan, phenylalanine or tyrosine.

  揭示了在原核细胞中具有抗生素特性的蛋氨酸类似物。这些类似物与一个或多个可选择替代的氨基酸偶联，其中至少一个氨基酸是苯基甘氨酸、色氨酸、苯丙氨酸或酪氨酸。
• [EN] 2-PYRIDYL CARBOXAMIDE-CONTAINING SPLEEN TYROSINE KINASE (SYK) INHIBITORS<br/>[FR] INHIBITEURS DE TYROSINE KINASE DE LA RATE (SYK) CONTENANT UN 2-PYRIDYL CARBOXAMIDE
  申请人：MERCK SHARP & DOHME

  公开号：WO2013052394A1

  公开（公告）日：2013-04-11

  The invention provides certain 2-pyridyl carboxamide-containing compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein A and B are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions mediated by Spleen Tyrosine Kinase (Syk) kinase.

  本发明提供了一些含有2-吡啶甲酰胺的化合物，其化学式为(I)或药用可接受的盐，其中A和B按本发明定义。本发明还提供了包含这些化合物的药物组合物，以及使用这些化合物来治疗由脾酪氨酸激酶（Syk）介导的疾病或状况的方法。
• Chemoselective Synthesis of Carbamates using CO₂as Carbon Source
  作者：Daniel Riemer、Pradipbhai Hirapara、Shoubhik Das

  DOI：10.1002/cssc.201600521

  日期：2016.8.9

  Synthesis of carbamates directly from amines using CO2 as the carbon source is a straightforward and sustainable approach. Herein, we describe a highly effective and chemoselective methodology for the synthesis of carbamates at room temperature and atmospheric pressure. This methodology can also be applied to protect the amino group in amino acids and peptides, and also to synthesize important pharmaceuticals

  使用CO 2作为碳源直接从胺合成氨基甲酸酯是一种简单而可持续的方法。在此，我们描述了一种在室温和大气压下合成氨基甲酸酯的高效且化学选择性的方法。该方法还可用于保护氨基酸和肽中的氨基，也可用于合成重要的药物。
• ANTIBIOTIC AMINO ACID MIMETICS
  申请人：BIOXINESS PHARMACEUTICALS, INC.

  公开号：US20180282271A1

  公开（公告）日：2018-10-04

  Disclosed are methionine mimetic compounds that possess antibiotic properties in prokaryotic cells. The compounds of this invention comprise a dipeptide having a methionine mimetic bound to an aromatic amino acid. Such compounds exhibit significantly improved antibacterial properties.

  本发明揭示了在原核细胞中具有抗生素特性的蛋氨酸类似化合物。该发明的化合物包括一个含有蛋氨酸类似物与芳香族氨基酸结合的二肽。这类化合物表现出明显改善的抗菌特性。
• ANTIBIOTIC OLIGOPEPTIDE MIMETICS
  申请人：BIOXINESS PHARMACEUTICALS, INC.

  公开号：US20180340008A1

  公开（公告）日：2018-11-29

  Disclosed are amino acid mimetics that possess antibiotic properties in prokaryotic cells. These mimetics are coupled to one or more optionally substituted amino acids provided that at least one of the amino acids is an optionally substituted amino acid selected from the group consisting of phenylglycine, tryptophan, phenylalanine, histidine, and tyrosine.

  揭示了在原核细胞中具有抗生素特性的氨基酸类似物。这些类似物与一个或多个可选择取代的氨基酸偶联，其中至少一个氨基酸是从苯基甘氨酸、色氨酸、苯丙氨酸、组氨酸和酪氨酸所组成的群中选择的可选择取代的氨基酸。