dimethyl benzoyl-D-aspartate | 1562416-43-6

• 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: dimethyl benzoyl-D-aspartate
• 英文别名: dimethyl (2R)-2-benzamidobutanedioate
• CAS: 1562416-43-6
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: JAGPKJXEMSRCQL-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl benzoyl-D-aspartate 在 盐酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.67h， 生成 D-threo-3-hydroxyaspartic acid dimethyl ester hydrochloride
  参考文献：
  名称：

  Plusbacin A3的固相全合成

  摘要：

  公开了使用固相肽合成(SPPS)的缩肽天然产物加杆菌素A 3 ( 1 )的全合成。通过非对映选择性 Joullié-Ugi 三组分反应 (JU-3CR)/水解序列制备了与 Fmoc SPPS 相容的 3-羟基-脯氨酸衍生物。在固相支持物上肽延伸后，肽从树脂上裂解，然后大环内酰胺化和整体去保护，得到plusbacin A 3 ( 1 )。

  DOI：

  10.1021/acs.orglett.2c00667
• 作为产物：
  描述：

  N-苯甲酰基-L-天门冬氨酸 4-甲酯 在 Boc-Dmaa-D-pro-Aic-Ser(Bn)-NMe₂ 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 dimethyl benzoyl-D-aspartate 、 dimethyl benzoyl-L-aspartate
  参考文献：
  名称：

  Peptide-Catalyzed Conversion of Racemic Oxazol-5(4H)-ones into Enantiomerically Enriched α-Amino Acid Derivatives

  摘要：

  We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

  DOI：

  10.1021/jo402828f

文献信息

• 10.1016/j.tetlet.2024.155177
  作者：Katayama, Yuto、Nishikawa, Yudai、Inagaki, Minoru、Park, Jiyoon、Oh, Dong-Chan、Masuda, Yuichi

  DOI：10.1016/j.tetlet.2024.155177

  日期：——

  This paper reports the total synthesis of antibacterial cyclic hexapeptides nicrophorusamides A () and B (), isolated from the actinomycete strain UTG9 belonging to the genus . The synthesis involved solid-phase peptide elongation and solution-phase macrolactamization, followed by the removal of the protecting groups. Synthetic and demonstrated inhibitory effects on the growth of with minimum inhibitory

  本文报道了从放线菌UTG9属中分离得到的抗菌环六​​肽硝基磷酰胺A()和B()的全合成。合成涉及固相肽延伸和溶液相大环内酰胺化，然后除去保护基团。使用肉汤微量稀释法测定的合成和证明的生长抑制作用，最小抑制浓度 (MIC) 值分别为 8 μg/mL 和 16 μg/mL。
• Peptide-Catalyzed Conversion of Racemic Oxazol-5(4<i>H</i>)-ones into Enantiomerically Enriched α-Amino Acid Derivatives
  作者：Anthony J. Metrano、Scott J. Miller

  DOI：10.1021/jo402828f

  日期：2014.2.21

  We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.
• Solid-Phase Total Synthesis of Plusbacin A₃
  作者：Kazuki Takashina、Akira Katsuyama、Rintaro Kaguchi、Kazuki Yamamoto、Toyotaka Sato、Satoshi Takahashi、Motohiro Horiuchi、Shin-ichi Yokota、Satoshi Ichikawa

  DOI：10.1021/acs.orglett.2c00667

  日期：2022.3.25

  The total synthesis of the depsipeptide natural product plusbacin A3 (1) utilizing solid-phase peptide synthesis (SPPS) was disclosed. A 3-hydroxy-proline derivative compatible with Fmoc SPPS was prepared by a diastereoselective Joullié–Ugi three-component reaction (JU-3CR)/hydrolysis sequence. After peptide elongation on the solid support, cleavage of the peptide from the resin, followed by macrolactamization

  公开了使用固相肽合成(SPPS)的缩肽天然产物加杆菌素A 3 ( 1 )的全合成。通过非对映选择性 Joullié-Ugi 三组分反应 (JU-3CR)/水解序列制备了与 Fmoc SPPS 相容的 3-羟基-脯氨酸衍生物。在固相支持物上肽延伸后，肽从树脂上裂解，然后大环内酰胺化和整体去保护，得到plusbacin A 3 ( 1 )。