H-(D-Ala)2-OMe | 76572-04-8

• 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: H-(D-Ala)2-OMe
• 英文别名: methyl (2R)-2-[(2R)-2-aminopropanamido]propanoate；methyl (2R)-2-[[(2R)-2-aminopropanoyl]amino]propanoate
• CAS: 76572-04-8
• 化学式: C₇H₁₄N₂O₃
• 分子量: 174.2
• InChiKey: LNLRCQQTGATDQI-RFZPGFLSSA-N

物化性质

• 沸点：
  301.4±22.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H-(D-Ala)2-OMe 在 Streptomyces spp. 83D₁₂ D-aminopeptidase 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 生成 D-丙氨酰-D-丙氨酸
  参考文献：
  名称：

  Aminolytic reaction catalyzed by d-stereospecific amidohydrolases from Streptomyces spp

  摘要：

  From investigation of 2000 soil isolates, we identified two serine-type amidohydrolases that can hydrolyze D-aminoacyl derivatives from the culture supernatant of Streptomyces species 82F2 and 83D12. The enzymes, redesignated as 82F2-DAP and 83D12-DAP, were purified for homogeneity and characterized. Each enzyme had molecular mass of approximately 40 kDa, and each showed moderate stability with respect to temperature and pH. Among hydrolytic activities toward D-aminoacyl-pNAs, the enzymes showed strict specificity toward D-Phe-pNA, but showed broad specificity toward D-aminoacyl esters. The specific activity for D-Phe-pNA hydrolysis of 82F2-DAP was ten-fold higher than that of 83D12-DAP. As a second function, each enzyme showed peptide bond formation activity by its function of aminolysis reaction. Based on results of D-Phe D-Phe synthesis under various conditions, we propose a reaction mechanism for D-Phe D-Phe production. Furthermore, the enzymes exhibited peptide elongation activity, producing oligo homopeptide in a one-pot reaction. We cloned the genes encoding each enzyme, which revealed that the primary structure of each enzyme showed 30-60% identity with those of peptidases belonging to the clan SE, S12 peptidase family categorized as serine peptidase with D-stereospecificity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2011.04.020
• 作为产物：
  描述：

  N-[(苯基甲氧基)羰基]-D-丙氨酰-D-丙氨酸甲酯 在 hydrogenation catalyst 氢气 作用下， 以 甲醇 为溶剂， 生成 H-(D-Ala)2-OMe
  参考文献：
  名称：

  来自手性Cα ，α-二取代甘氨酸的肽。同手性（MeMe）Leu / Ala模型肽的合成和构象分析

  摘要：

  通过溶液法合成了手性（αMe）Leu / Ala和Leu / Ala模型肽并进行了充分表征。使用FT-IR吸收和1 H NMR进行三肽的溶液构象分析。通过X射线衍射解析ZD-（αMe）Leu-（D-Ala）2 -OMe一水合物的晶体状态结构。获得的结果支持以下结论：未编码的（αMe）Leu残基折叠成β弯曲和螺旋结构的趋势明显高于其未甲基化的蛋白质对应物（Leu）。

  DOI：

  10.1002/recl.19941130104

文献信息

• Effect of Stereochemistry on Chirality and Gelation Properties of Supramolecular Self‐Assemblies
  作者：Minggao Qin、Yaqian Zhang、Chao Xing、Li Yang、Changli Zhao、Xiaoqiu Dou、Chuanliang Feng

  DOI：10.1002/chem.202004533

  日期：2021.2.10

  by the amino acid adjacent to the benzene core, irrespective of the absolute configuration of the C‐terminal amino acid. In addition, molecular chirality also has a significant influence on the gelation behavior. For the diphenylalanine‐based gelators, the homochiral gelators can be gelled through a conventional heating–cooling process, whereas heterochiral gelators form translucent stable gels under

  尽管已经在各种结构水平上制备了手性纳米结构，但是手性从分子到超分子自组装的转移和扩增仍然令人费解，特别是对于杂手性分子而言。在此，C 2的四个系列设计并合成了具有各种氨基酸序列和不同手性的基于对称二肽的衍生物。实现了分子手性向超分子组装体的转录和扩增。结果表明，超分子手性仅由与苯核心相邻的氨基酸决定，而与C端氨基酸的绝对构型无关。另外，分子手性也对胶凝行为具有重要影响。对于基于二苯丙氨酸的胶凝剂，同手性胶凝剂可以通过常规的加热-冷却过程进行胶凝，而异手性胶凝剂在超声处理下形成半透明的稳定凝胶。外消旋凝胶比纯对映异构体具有更高的机械性能。
• Introducing A New Class of Sulfonyl Fluoride Hubs via Radical Chloro‐Fluorosulfonylation of Alkynes
  作者：Xingliang Nie、Tianxiao Xu、Yuhao Hong、Honghai Zhang、Chenxi Mao、Saihu Liao

  DOI：10.1002/anie.202109072

  日期：2021.9.27

  Sulfonyl fluorides have widespread applications in many important fields, including ligation chemistry, chemical biology, and drug discovery. Therefore, new methods to increase the synthetic efficiency and expand the available structures of sulfonyl fluorides are highly in demand. Here, we introduce a new and powerful class of sulfonyl fluoride hubs, β-chloro alkenylsulfonyl fluorides (BCASF), which

  磺酰氟在许多重要领域有着广泛的应用，包括连接化学、化学生物学和药物发现。因此，迫切需要提高合成效率和扩展磺酰氟可用结构的新方法。在这里，我们介绍了一类新的强大的磺酰氟中心，β-氯烯基磺酰氟（BCASF），它可以在光氧化还原条件下通过炔烃的自由基氯氟磺酰基双官能化来构建。BCASF 分子表现出多种反应性，并在氯化物位点进行一系列转化，同时保持磺酰氟基团的完整性，包括还原、Suzuki 偶联、Sonogashira 偶联以及与各种氮、氧和硫亲核试剂的亲核取代。顺式烯基磺酰氟、二烯基磺酰氟和炔基磺酰氟，它们在以前用已知方法合成是具有挑战性的，甚至是不可能的。此外，还证明了 BCASF 在肽和药物的后期修饰中的进一步应用。
• Switchable Amplification of Vibrational Circular Dichroism as a Probe of Local Chiral Structure
  作者：Sérgio R. Domingos、Hans J. Sanders、František Hartl、Wybren J. Buma、Sander Woutersen

  DOI：10.1002/anie.201407376

  日期：2014.12.15

  A new method to detect the vibrational circular dichroism (VCD) of a localized part of a chiral molecular system is reported. A local VCD amplifier was implemented, and the distance dependence of the amplification was investigated in a series of peptides. The results indicate a characteristic distance of 2.0±0.3 bonds, which suggests that the amplification is a localized phenomenon. The amplifier can

  报道了一种检测手性分子系统局部的振动圆二色性（VCD）的新方法。实现了本地VCD放大器，并在一系列肽中研究了扩增的距离依赖性。结果表明特征距离为2.0±0.3个键，这表明扩增是局部现象。放大器可以与分子的特定部分共价偶联，并且可以通过电化学方式打开和关闭。通过减去放大器处于ON和OFF状态时获得的VCD频谱，可以将放大器本地环境的VCD与总VCD频谱分开。因此，可切换的本地VCD放大使“放大”手性分子的特定部分成为可能。
• Peptides from chiral Cα,α-disubstituted glycines. Synthesis and conformational analysis of homochiral (αMe) Leu / Ala model peptides
  作者：J. Kamphuis、W. H. J. Boesten、H. E. Schoemaker、A. Aubry、D. Bayeul、A. Dautant、M. Pantano、F. Formaggio、M. Crisma、G. M. Bonora、C. Toniolo

  DOI：10.1002/recl.19941130104

  日期：——

  Homochiral (αMe)Leu/Ala and Leu/Ala model peptides were synthesized by solution methods and fully characterized. A solution conformational analysis of the tripeptides was carried out using FT-IR absorption and 1H NMR. The crystal-state structure of Z-D-(αMe)Leu-(D-Ala)2-OMe monohydrate was resolved by X-ray diffraction. The results obtained support the conclusion that the tendency of the non-coded

  通过溶液法合成了手性（αMe）Leu / Ala和Leu / Ala模型肽并进行了充分表征。使用FT-IR吸收和1 H NMR进行三肽的溶液构象分析。通过X射线衍射解析ZD-（αMe）Leu-（D-Ala）2 -OMe一水合物的晶体状态结构。获得的结果支持以下结论：未编码的（αMe）Leu残基折叠成β弯曲和螺旋结构的趋势明显高于其未甲基化的蛋白质对应物（Leu）。
• Direct synthesis of β^2,3‐amino acid from β‐hydroxycarbamides: Implication in the synthesis of azumamide analogs and conformational analysis
  作者：Afsar Ali Khan、Jayanti Vaishnav、Manoj Kumar Gangwar、Ravi Sankar Ampapathi、Dipankar Koley

  DOI：10.1002/jhet.4717

  日期：2023.11

  The designed β2,3 unnatural amino acids have been synthesized from α-methyl-β-hydroxycarbamides via direct azidation without obtaining eliminated products. Furthermore, these β2,3 amino acids were utilized to synthesize cyclic tetrapeptides (CTPs) as azumamide analogs. 2D-NMR analysis revealed the compact secondary structure as a single conformer. Presence of intramolecular H-bonding in CTPs was observed

  所设计的β 2,3非天然氨基酸是由α-甲基-β-羟基脲通过直接叠氮化合成的，没有获得消除的产物。此外，这些 β2,3氨基酸被用来合成环状四肽（CTP）作为 azumamide 类似物。二维核磁共振分析揭示了紧凑的二级结构为单一构象异构体。在这种 α 3 β 2,3结构中观察到 CTP 中存在分子内氢键，并显示出七元 γ 转角结构。