2-amino-2-methylpropionic acid methyl ester | 13257-67-5

• 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: 2-amino-2-methylpropionic acid methyl ester
• 英文别名: methyl 2-amino-2-methylpropanoate
• CAS: 13257-67-5
• 化学式: C₅H₁₁NO₂
• mdl: MFCD12407415
• 分子量: 117.148
• InChiKey: HMZHEECHJWHZJX-UHFFFAOYSA-N

物化性质

• 熔点：
  186.5-187 °C
• 沸点：
  120.6±13.0 °C(Predicted)
• 密度：
  0.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990
• 包装等级：
  III
• 危险类别：
  3,8
• 危险性防范说明：
  P210,P280,P305+P351+P338,P310
• 危险品运输编号：
  2924
• 危险性描述：
  H225,H314
• 储存条件：
  存储条件为2-8°C，避免光照，并在惰性气体环境中保存。

反应信息

• 作为反应物：
  描述：

  2-amino-2-methylpropionic acid methyl ester 在 三乙胺 、 三氟甲烷磺酸甲酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-甲基丙氨酸
  参考文献：
  名称：

  Heterocyclic aromatic compounds useful as growth hormone secretagogues

  摘要：

  提供了一些对激发内源性生长激素的产生或释放以及治疗肥胖、骨质疏松（改善骨密度）和改善肌肉质量和肌肉力量有用的杂环芳香化合物。 这些杂环芳香化合物具有以下结构，包括其药用可接受的盐和所有立体异构体， 其中Xa是杂芳基，最好是，  而R1、R1a、R6、Y、Xb、A、B、Z、R3、R4、R4a、R5和R5a的定义如下。

  公开号：

  US06525203B1
• 作为产物：
  描述：

  2-氨基异丁酸甲酯盐酸盐 在 anion exchange resin 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以79%的产率得到2-amino-2-methylpropionic acid methyl ester
  参考文献：
  名称：

  利用工业阴离子交换树脂介导的受保护氨基酸卤化物合成肽

  摘要：

  摘要描述了由商业阴离子交换树脂介导的用于肽的溶液相合成的受保护氨基酸卤化物（氯化物，氟化物）的偶联。该反应在有机介质中进行，从而避免了使用有机碱或无机碱。联轴器快速，清洁且无外消旋。阴离子交换树脂起着固相碱性清除剂的作用，吸收产生的HCl，并使胺发生反应。该方法被扩展用于空间位阻的α，α，-二烷基氨基酸的偶联。 图形概要

  DOI：

  10.1007/s10989-012-9337-5
• 作为试剂：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 sodium hydroxide 、 N-羟基丁二酰亚胺 、 2-amino-2-methylpropionic acid 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
  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

• Supramolecular tryptophan-zipper forms a tripeptide as a regular proton transporter
  作者：Debasish Podder、Supriya Sasmal、Krishnendu Maji、Debasish Haldar

  DOI：10.1039/c5ce02005k

  日期：——

  The diverse structure and assembly of two peptide analogues have been investigated. The tripeptide containing tryptophan, α-aminoisobutyric acid and valine self-assembles through various noncovalent interactions to form a tryptophan-zipper-like structure by intermolecular hydrogen bonding and π–π interactions. But the leucine analogue adopts a water-mediated hydrogen-bonded cage-like structure. X-ray crystallography shed some light on the structure of the tryptophan-zipper at the atomic level. Moreover, in U-tube experiments using pH gradient as the driving force across a liquid chloroform phase, the supramolecular tryptophan-zipper acts as a passive regular proton transporter.

  两种肽类似物的多样性结构和组装方式已被研究。含色氨酸、α-氨基异丁酸和缬氨酸的三肽通过各种非共价相互作用自组装，形成类似色氨酸拉链结构，这种结构依赖于分子间氢键和π-π相互作用。然而，亮氨酸类似物则形成一种由水介导的氢键笼状结构。X射线晶体学在原子层面上揭示了色氨酸拉链结构的某些信息。此外，在利用pH梯度作为推动力穿过氯仿液相的U型管实验中，超分子色氨酸拉链起到了被动规则性质子载体的作用。
• A step-economic and one-pot access to chiral C^α-tetrasubstituted α-amino acid derivatives <i>via</i> a bicyclic imidazole-catalyzed direct enantioselective <i>C</i>-acylation
  作者：Mo Wang、Muxing Zhou、Lu Zhang、Zhenfeng Zhang、Wanbin Zhang

  DOI：10.1039/d0sc00808g

  日期：——

  Cα-Tetrasubstituted α-amino acids are ubiquitous and unique structural units in bioactive natural products and pharmaceutical compounds. The asymmetric synthesis of these molecules has attracted a lot of attention, but a more efficient method is still greatly desired. Here we describe the first sequential four-step acylation reaction for the efficient synthesis of chiral Cα-tetrasubstituted α-amino acid derivatives

  Ç α -Tetrasubstitutedα氨基酸是生物活性天然产物和药物化合物普遍存在的，并且独特的结构单元。这些分子的不对称合成引起​​了很多关注，但是仍然非常需要一种更有效的方法。在这里，我们描述了用于手性C的有效合成的第一顺序四步酰化反应α -tetrasubstitutedα氨基从简单的酸衍生物Ñ -acylated氨基酸通过使用单一亲核催化剂的自动串联催化。通过直接对映选择性C-酰化提高了合成效率。该方法得出相应的Cα具有优良对映选择性（高达99％ee）的-四取代α-氨基酸衍生物。这种循序渐进，一锅又自动串联的策略可以轻松访问重要的手性结构单元，例如肽，丝氨酸和恶唑啉，它们经常用于药物和合成化学中。
• [EN] HYDANTOIN CONTAINING DEOXYURIDINE TRIPHOSPHATASE INHIBITORS<br/>[FR] HYDANTOÏNE CONTENANT DES INHIBITEURS DE LA DÉSOXYURIDINE TRIPHOSPHATASE
  申请人：CV6 THERAPEUTICS NI LTD

  公开号：WO2018098206A1

  公开（公告）日：2018-05-31

  Provided herein are dUTPase inhibitors, compositions comprising such compounds and methods of using such compounds and compositions.

  提供的是dUTPase抑制剂，包含此类化合物的组合物以及使用此类化合物和组合物的方法。
• [EN] PYRIDIN- 2 -AMIDES USEFUL AS CB2 AGONISTS<br/>[FR] PYRIDIN-2-AMIDES UTILES COMME AGONISTES DE CB2
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012168350A1

  公开（公告）日：2012-12-13

  The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

  本发明涉及式(I)的化合物，其中R1至R4的定义如描述和权利要求中所述。式(I)的化合物可以用作药物。
• Dipeptide analogs for treating conditions associated with amyloid fibril formation
  申请人：Gazit Ehud

  公开号：US09096645B2

  公开（公告）日：2015-08-04

  Dipeptide analogs comprising a tryptophan (Trp) moiety coupled to a beta-sheet breaker moiety derived from alpha-aminoisobutyric acid (Aib) are disclosed. The dipeptide analogs exhibit an improved performance in inhibiting amyloid fibril formation, as compared to previously described dipeptides. Compositions containing the dipeptide analogs and uses thereof in treating amyloid-associated diseases and disorders are also disclosed.

  披露了包含色氨酸（Trp）结构域与源自α-氨基异丁酸（Aib）的β-折叠破坏剂结构域偶联的二肽类似物。与之前描述的二肽相比，这些二肽类似物在抑制淀粉样纤维形成方面表现出更好的性能。还披露了含有这些二肽类似物的组合物，以及它们在治疗与淀粉样蛋白相关疾病和障碍中的应用。