BOC-Asp(OBzl)-Asp(OBzl)-OBzl | 104870-31-7

• 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: BOC-Asp(OBzl)-Asp(OBzl)-OBzl
• 英文别名: dibenzyl (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-phenylmethoxybutanoyl]amino]butanedioate
• CAS: 104870-31-7
• 化学式: C₃₄H₃₈N₂O₉
• 分子量: 618.684
• InChiKey: VHBFGDHYGBFPTP-NSOVKSMOSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  776.1±60.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  45.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  146.33
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  BOC-Asp(OBzl)-Asp(OBzl)-OBzl 在 palladium on activated charcoal TEA 、 氢气 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 反应 3.0h， 生成 N^α-lauryl-L-aspartyl-L-aspartic acid
  参考文献：
  名称：

  Gaur, R. K.; Chauhan, V. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 405 - 408

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 、 L-aspartic acid dibenzyl ester hydrochloride 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以70%的产率得到BOC-Asp(OBzl)-Asp(OBzl)-OBzl
  参考文献：
  名称：

  Solvent effects on the redox properties of ferrocenoyl-dipeptides

  摘要：

  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。

  DOI：

  10.1039/b005125j

文献信息

• Dipeptides as Leaving Group in the Enzyme-Catalyzed DNA Synthesis
  作者：Xiao-Ping Song、Camille Bouillon、Eveline Lescrinier、Piet Herdewijn

  DOI：10.1002/cbdv.201200261

  日期：2012.12

  polymerases. Although the incorporation efficiency is not very high, it demonstrates that some of these dipeptides can be accommodated in the active site of polymerases and function as leaving groups in the enzymatic synthesis of DNA.

  2'-脱氧腺苷单磷酸与二肽的结合物已经合成，并作为几种聚合酶的底物进行了测试。尽管掺入效率不是很高，但是表明这些二肽中的一些可以被容纳在聚合酶的活性位点中并在DNA的酶促合成中用作离去基团。
• 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。
• [EN] PEPTIDE COMPOSITIONS FOR SLOWING DEGRADATION OF VITAMIN-MINERAL SUPPLEMENTS, FOODS, PHARMACEUTICALS, AND COSMETICS<br/>[FR] COMPOSITIONS PEPTIDIQUES POUR RALENTIR LA DÉGRADATION DE COMPLÉMENTS DE VITAMINES ET DE MINÉRAUX, D'ALIMENTS, DE PRODUITS PHARMACEUTIQUES ET COSMÉTIQUES
  申请人：BAILEY STEVEN W

  公开号：WO2019112630A1

  公开（公告）日：2019-06-13

  Compositions of foods, vitamin and mineral supplements, topical or oral drugs, and cosmetic products containing a small peptide or peptides for slowing degradation, for example by transition metals. The peptides are di, tri, terra-, and/or penta-peptides containing two or more aspartic acid residues. The degradation of several of the vitamin and other constituents vitamin-mineral supplements can be considerably slowed by composition incorporating such peptides, particularly if soluble (and thus bioavailable) forms of copper and/or iron are also present. The peptides can be hydrolyzed by the normal digestive process thus releasing bound metals. Multiple aspartate peptide(s) compositions with foods, topical or oral drugs, cosmetic, and hair care products can replace synthetic chelating preservative agents. Methods are also described to effectively slow degradation and preserve the above products using multiple aspartate peptides.

  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。
• 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.
• SUBASINGHE, NALIN;SCHULTE, MARVIN;CHAN, MICHAEL Y. -M.;ROON, ROBERT J.;KO+, J. MED. CHEM., 33,(1990) N0, C. 2734-2744
  作者：SUBASINGHE, NALIN、SCHULTE, MARVIN、CHAN, MICHAEL Y. -M.、ROON, ROBERT J.、KO+

  DOI：——

  日期：——