2-(2-氨基丙酰氨基)丙酸 | 1115-78-2

• 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: 2-(2-氨基丙酰氨基)丙酸
• 中文别名: H-丙氨酸-D-丙氨酸羟基
• 英文名称: (S)-2-((R)-2-Amino-propionylamino)-propionic acid
• 英文别名: D-Alanyl-L-alanine；H-D-Ala-L-Ala-OH；D-Ala-L-Ala；N-D-alanyl-L-alanine；N-D-Alanyl-L-alanin；(2S)-2-[[(2R)-2-azaniumylpropanoyl]amino]propanoate
• CAS: 1115-78-2
• 化学式: C₆H₁₂N₂O₃
• 分子量: 160.173
• InChiKey: DEFJQIDDEAULHB-DMTCNVIQSA-N

物化性质

• 熔点：
  275-276 °C
• 沸点：
  402.6±30.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924199090
• 储存条件：
  -15°C

制备方法与用途

D-Ala-Ala 是一种肽。

反应信息

• 作为反应物：
  描述：

  2-(2-氨基丙酰氨基)丙酸 在 recombinant Streptomyces coelicolor Sco₃₀₅₈ dipeptidase 、 水 作用下， 生成 L-丙氨酸 、 D-丙氨酸
  参考文献：
  名称：

  Structure, Mechanism, and Substrate Profile for Sco3058: The Closest Bacterial Homologue to Human Renal Dipeptidase,

  摘要：

  Human renal dipeptidase, an enzyme associated With glutathione metabolism and the hydrolysis of beta-lactams, is similar in sequence to a cluster of similar to 400 microbial proteins currently annotated as nonspecific dipeptidases within the amidohydrolase superfamily. The closest homologue to the human renal dipeptidase from a Fully sequenced microbe is Sco3058 from Streptomyces coelicolor. Dipeptide Substrates of Sco3058 were identified by screening a comprehensive series Of L-Xaa-L-Xaa, L-Xaa-D-Xaa, and D-Xaa-L-Xaa dipeptide libraries. The substrate specificity profile shows that Sco3058 hydrolyzes a broad range of dipeptides with a marked preference for all L-amino acid at the N-terminus and a D-amino acid at the C-terminus. The best Substrate identified was L-Arg-D-Asp (k(eat)/K-m = 7.6 x 10(5) M-1 s(-1)). The three-dimensional structure of Sco3058 was determined in the absence and presence of the inhibitors citrate and a phosphinate mimic Of L-Ala-D-Asp. The enzyme folds as (beta/alpha)(8) barrel, and two zinc Ions are bound in the active site. Site-directed mutagenesis was used to probe the importance of specific residues that have direct interactions with the substrate analogues in the active site (Asp-22, His-150, Arg-223, and Asp-320). The solvent viscosity and kinetic effects of D2O indicate that Substrate binding is relatively sticky and that proton transfers do not occur during the rate-limiting step. A bell-shaped pH-rate profile for k(cat) and k(cat)/k(m) indicated that one group needs to he deprotonated and a second group Must be protonated for optimal turnover. Computational docking of high-energy intermediate forms Of L/D-Ala-L/D-Ala to the three-dimensional Structure of Sco3058 identified the Structural determinants for the stereochemical preferences for Substrate binding and turnover.

  DOI：

  10.1021/bi901935y
• 作为产物：
  描述：

  FMOC-D-Ala-L-AlaOMe 在 dimethylsulfoxonium methylide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 2-(2-氨基丙酰氨基)丙酸
  参考文献：
  名称：

  甲基亚砜基二甲亚砜是同时脱保护N -Fmoc-α-氨基酸和N -Fmoc-肽酯的氨基和羧基官能团的唯一试剂

  摘要：

  二甲基亚砜基亚甲基被描述为用于同时脱去N -Fmoc-α-氨基酸和N -Fmoc-肽酯的氨基和羧基官能团的独特且有用的试剂。新方法已成功应用于溶液和固相肽合成。所采用的方法也成功地扩展到含有在侧链上带有酸敏感保护基的氨基酸的肽。此外，在N-Fmoc-二肽甲基酯与二甲基亚砜基甲基的脱保护反应中未观察到可测量的差向异构。

  DOI：

  10.1016/j.tet.2012.12.052

文献信息

• Epimerization of Cyclic Alanyl-Alanine in Basic Solutions
  作者：Toratane Munegumi、Takeshi Fujimoto、Michio Takada、Nozomi Nagashima

  DOI：10.13005/ojc/300103

  日期：2014.3.30

  Alanine anhydrides (Cyclo-(Ala-Ala)) are the simplest dipeptides that have two chiral centers and three diastereomers: Cyclo-(L-Ala-L-Ala), Cyclo-(D-Ala-D-Ala), and Cyclo-(L-Ala-D-Ala).Analysis of the epimerization of these peptides may throw light on the development of homochirality in proteins. We show that the epimerization rate of Cyclo-(L-Ala-L-Ala) and Cyclo-(D-Ala-D-Ala) is higher than that of Cyclo-(L-Ala-D-Ala), while the ring-opening rates of Cyclo-(L-Ala-L-Ala) and Cyclo-(D-Ala-D-Ala) arelower than that of Cyclo-(L-Ala-D-Ala) in basic aqueous solutions. The total reaction resulted in the preferred stability of Cyclo-(L-Ala-L-Ala) and Cyclo-(D-Ala-D-Ala) to Cyclo-(D-Ala-L-Ala).

  丙氨酸酐（环-(丙-丙)）是最简单的二肽，具有两个手性中心和三种非对映异构体：环-(L-丙-L-丙)、环-(D-丙-D-丙)和环-(L-丙-D-丙)。分析这些肽的差向异构化可能有助于揭示蛋白质中同手性的发展。我们表明，环-(L-丙-L-丙)和环-(D-丙-D-丙)的差向异构化速率高于环-(L-丙-D-丙)，而在碱性水溶液中，环-(L-丙-L-丙)和环-(D-丙-D-丙)的环开裂速率低于环-(L-丙-D-丙)。总反应导致了环-(L-丙-L-丙)和环-(D-丙-D-丙)相对于环-(D-丙-L-丙)的优先稳定性。
• Proteins and nucleic acids from meningitis/sepsis-associated Escherichia coli
  申请人：GlaxoSmithKline Biologicals SA

  公开号：US10035826B2

  公开（公告）日：2018-07-31

  Disclosed herein are various open reading frames from a strain of E. coli responsible for neonatal meningitis (MNEC), and a subset of these that is of particular interest for preparing compositions for immunizing against MNEC infections.

  本文公开了导致新生儿脑膜炎（MNEC）的大肠杆菌菌株的各种开放阅读框，以及其中对制备 MNEC 感染免疫组合物特别感兴趣的子集。
• Texturizing lactic acid bacteria strains
  申请人：CHR. HANSEN A/S

  公开号：US10392597B2

  公开（公告）日：2019-08-27

  The present invention relates to mutants of lactic acid bacteria which are resistant towards the antibiotic D-cycloserine and/or functionally equivalent antibiotics and which were found to give an increased texture when grown in milk while maintaining the other growth properties of the parent strain. The present invention, furthermore, relates to compositions comprising such mutants, and to dairy products fermented with the lactic acid bacteria resistant towards D-cycloserine and/or functionally equivalent antibiotics.

  本发明涉及对抗生素 D-环丝氨酸和/或功能相当的抗生素具有抗性的乳酸菌突变体，这些突变体在牛奶中生长时可增加质地，同时保持亲本菌株的其他生长特性。此外，本发明还涉及包含这种突变体的组合物，以及用对 D-环丝氨酸和/或功能相当的抗生素具有抗性的乳酸菌发酵的乳制品。
• Influence of Optically Active Acyl Groups on the Enzymatic Hydrolysis of N-Acylated-L-amino Acids
  作者：Shou-Cheng J. Fu、Sanford M. Birnbaum、Jesse P. Greenstein

  DOI：10.1021/ja01652a057

  日期：1954.12
• Dissociation Constants of Peptides. III. The Effect of Optical Configuration on the Infrared Spectra of Polyfunctional Peptides^1a,b
  作者：Eric Ellenbogen

  DOI：10.1021/ja01583a032

  日期：1956.1