H-Asp(OBzl)-Asp(OBzl)-OBzl | 118429-74-6

• 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: H-Asp(OBzl)-Asp(OBzl)-OBzl
• 英文别名: Asp-Asp tribenzyl ester；HAsp(OBzl)Asp(OBzl)2
• CAS: 118429-74-6
• 化学式: C₂₉H₃₀N₂O₇
• 分子量: 518.566
• InChiKey: LOAQGBXMKFZWSO-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  134.02
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  H-Asp(OBzl)-Asp(OBzl)-OBzl 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙二醇二甲醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 L-Asp-L-Asp-L-Asp-OH
  参考文献：
  名称：

  [EN] PEPTIDE COMPOSITIONS FOR SLOWING DEGRADATION OF VITAMIN-MINERAL SUPPLEMENTS, FOODS, PHARMACEUTICALS, AND COSMETICS
  [FR] COMPOSITIONS PEPTIDIQUES POUR RALENTIR LA DÉGRADATION DE COMPLÉMENTS DE VITAMINES ET DE MINÉRAUX, D'ALIMENTS, DE PRODUITS PHARMACEUTIQUES ET COSMÉTIQUES

  摘要：

  食物、维生素和矿物质补充剂、局部或口服药物，以及含有小肽或肽的化妆品产品，用于减缓降解，例如通过过渡金属。这些肽是含有两个或更多天冬氨酸残基的二肽、三肽、四肽和/或五肽。通过含有这些肽的组合，可以显著减缓多种维生素和其他成分维生素矿物质补充剂的降解，特别是如果可溶（因此生物有效）的铜和/或铁的形式也同时存在。这些肽可以通过正常的消化过程水解，从而释放结合的金属。含有多个天冬氨酸肽的食品、局部或口服药物、化妆品和护发产品可以取代合成螯合防腐剂。还描述了使用多个天冬氨酸肽有效减缓降解和保持上述产品的方法。

  公开号：

  WO2019112630A1
• 作为产物：
  描述：

  Boc-L-天门冬氨酸苄酯-Osu 在 盐酸 、 三乙胺 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.3h， 生成 H-Asp(OBzl)-Asp(OBzl)-OBzl
  参考文献：
  名称：

  [EN] PEPTIDE COMPOSITIONS FOR SLOWING DEGRADATION OF VITAMIN-MINERAL SUPPLEMENTS, FOODS, PHARMACEUTICALS, AND COSMETICS
  [FR] COMPOSITIONS PEPTIDIQUES POUR RALENTIR LA DÉGRADATION DE COMPLÉMENTS DE VITAMINES ET DE MINÉRAUX, D'ALIMENTS, DE PRODUITS PHARMACEUTIQUES ET COSMÉTIQUES

  摘要：

  食物、维生素和矿物质补充剂、局部或口服药物，以及含有小肽或肽的化妆品产品，用于减缓降解，例如通过过渡金属。这些肽是含有两个或更多天冬氨酸残基的二肽、三肽、四肽和/或五肽。通过含有这些肽的组合，可以显著减缓多种维生素和其他成分维生素矿物质补充剂的降解，特别是如果可溶（因此生物有效）的铜和/或铁的形式也同时存在。这些肽可以通过正常的消化过程水解，从而释放结合的金属。含有多个天冬氨酸肽的食品、局部或口服药物、化妆品和护发产品可以取代合成螯合防腐剂。还描述了使用多个天冬氨酸肽有效减缓降解和保持上述产品的方法。

  公开号：

  WO2019112630A1

文献信息

• Bone Targeting Prodrugs Based on Peptide Dendrimers, Synthesis and Hydroxyapatite Binding In Vitro
  作者：Liang Ouyang、Wencai Huang、Gu He、Li Guo

  DOI：10.2174/157017809788489981

  日期：2009.6.1

  Novel bone targeting naproxen prodrugs with poly(aspartic acid) moieties and with two and three poly(aspartic acid) sequences peptide dendrimers were synthesized using a conventional method. The modified naproxen conjugates were incubated with hydroxyapatite in PBS at physiological conditions over 16h. The study revealed the hydroxyapatite binding properties of poly(aspartic acid) and it was found that the peptide dendrimer prodrugs exhibited a faster initial binding and a greater total binding. The obtained binding data in vitro indicated that the peptide dendrimers with poly(aspartic acid) sequences were useful for the development of new bone targeting molecules for drug delivery to bone.

  通过常规方法合成了具有聚天冬氨酸部分和含有两条及三条聚天冬氨酸序列的肽树枝状大分子的非甾体抗炎药萘普生新型骨靶向前药。在生理条件下，将修饰的萘普生偶联物与羟基磷灰石在磷酸盐缓冲液中孵育16小时。研究发现聚天冬氨酸具有羟基磷灰石结合性质，并且发现含有聚天冬氨酸序列的肽树枝状大分子前药显示出更快的初始结合和更大的总结合。体外获得的结合数据表明，具有聚天冬氨酸序列的肽树枝状大分子在开发新的骨靶向药物递送分子方面具有应用价值。
• Solvent effects on the redox properties of ferrocenoyl-dipeptides
  作者：Murray V. Baker、Heinz-Bernhard Kraatz、J. Wilson Quail

  DOI：10.1039/b005125j

  日期：——

  The preparation and characterization of the novel ferrocenoyl-dipeptides, Fc-Asp(OBzl)-Asp(OBzl)-OBzl (5), Fc-Asp(OBzl)-Glu(OEt)-OEt (6) and Fc-Asp(OBzl)-Cys(Bzl)-OMe (7) are reported. In addition, Fc-Asp(OBzl)-OBzl (4) and its free acid, Fc-Asp(OH)-OH (8), were prepared. A crystal structure determination of 8 revealed an extensive H-bonding network involving a solvent molecule and adjacent molecules of 8 and suggests that these complexes are able to form strong hydrogen bonds with solvent molecules. All compounds show reversible one-electron oxidations in solution. The half-wave potential is strongly influenced by the nature of the solvent and correlates with the hydrogen donor ability α of the Kamlet–Taft formalism.

  报告了新型二茂铁酰基二肽 Fc-Asp(OBzl)-Asp(OBzl)-OBzl (5)、Fc-Asp(OBzl)-Glu(OEt)-OEt (6) 和 Fc-Asp(OBzl)-Cys(Bzl)-OMe (7) 的制备和表征。此外，还制备了 Fc-Asp(OBzl)-OBzl (4) 及其游离酸 Fc-Asp(OH)-OH (8)。8 的晶体结构测定显示，8 的溶剂分子和相邻分子之间存在广泛的氢键网络，这表明这些复合物能够与溶剂分子形成强氢键。所有化合物在溶液中都显示出可逆的单电子氧化作用。半波电势受溶剂性质的影响很大，并与 Kamlet-Taft 公式中的氢供体能力 α 相关。
• Synthesis of acyclic and dehydroaspartic acid analogs of Ac-Asp-Glu-OH and their inhibition of rat brain N-acetylated .alpha.-linked acidic dipeptidase (NAALA dipeptidase)
  作者：Nalin Subasinghe、Marvin Schulte、Michael Y. M. Chan、Robert J. Roon、James F. Koerner、Rodney L. Johnson

  DOI：10.1021/jm00172a009

  日期：1990.10

  The following structural and conformationally constrained analogues of Ac-Asp-Glu-OH (1) were synthesized: Ac-Glu-Glu-OH (2), Ac-D-Asp-Glu-OH (3), Ac-Glu-Asp-OH (4), Ac-Asp-Asp-OH (5), Ac-Asp-3-aminohexanedioic acid (6), Ac-3-amino-3-(carboxymethyl)propanoyl-Glu-OH (7), N-succinyl-Glu-OH (8), N-maleyl-Glu-OH (9), N-fumaryl-Glu-OH (10), and Ac-delta ZAsp-Glu-OH (11). These analogues were evaluated for their ability to inhibit the hydrolysis of Ac-Asp-[3,4-3H]-Glu-OH by N-acetylated alpha-linked acidic dipeptidase (NAALA dipeptidase) in order to gain some insight into the structural requirements for the inhibition of this enzyme. Analogues 4-6 and 9 were very weak inhibitors of NAALA dipeptidase (Ki greater than 40 microM), while 2, 3, and 7 with Ki values ranging from 3.2-8.5 microM showed intermediate inhibitory activity. The most active inhibitors of NAALA dipeptidase were compounds 8, 10, and 11 with Ki values of 0.9, 0.4, and 1.4 microM, respectively. These results suggest that the relative spacing between the side chain carboxyl and the alpha-carboxyl group of the C-terminal residue may be important for binding to the active site of the enzyme. They also indicate that the chi 1 torsional angle for the aspartyl residue is in the vicinity of 0 degrees.
• Carbonic anhydrase activators: Human isozyme II is strongly activated by oligopeptides incorporating the carboxyterminal sequence of the bicarbonate anion exchanger AE1
  作者：Andrea Scozzafava、Claudiu T Supuran

  DOI：10.1016/s0960-894x(02)00121-x

  日期：2002.4

  Di-/tri- and especially tetrapeptides incorporating the sequence DADD present in the carboxyterminal region of the bicarbonate, chloride anion exchanger AE1 strongly activate human carbonic anhydrase (CA) isozyme II, whereas they act as more inefficient activators of isozymes I and IV. This discovery suggests that in the metabolon hCA II-AE1. the last protein plans a role both as a CA activator as well as a bicarbonate transporter. A synthesis of the tripeptide DAD and the tetrapeptide DADD is also presented together with the possible explanation why such highly acidic oligopeptides efficiently bind to hCA II but not to the closely related isozymes I and IV. (C) 2002 Elsevier Science Ltd. All rights reserved.