benzyl (3S)-4-{[2-(benzyloxy)-2-oxoethyl]amino}-3-[(tert-butoxycarbonyl)amino]-4-oxobutanoate | 68802-35-7

• 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: benzyl (3S)-4-{[2-(benzyloxy)-2-oxoethyl]amino}-3-[(tert-butoxycarbonyl)amino]-4-oxobutanoate
• 英文别名: Boc-Asp(OBzl)-Gly-OBzl
• CAS: 68802-35-7
• 化学式: C₂₅H₃₀N₂O₇
• 分子量: 470.522
• InChiKey: PPDVSRUPJHVGLR-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  120.03
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  benzyl (3S)-4-{[2-(benzyloxy)-2-oxoethyl]amino}-3-[(tert-butoxycarbonyl)amino]-4-oxobutanoate 在 盐酸 、 N-羟基丁二酰亚胺 、 二甲基硫 、 三氟甲磺酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 67.0h， 生成 hydrocortisone-21-O-β-carbonylpropionyl-Glu-Asp-Gly-OH
  参考文献：
  名称：

  The synthesis and immunosuppressive activities of steroid–urotoxin linkers

  摘要：

  The urotoxins (Glu-Asp-Gly-OH, His-Gly-Glu-OH, His-Gly-Lys-OH, and His-Gly-Lys-NHNH2) were introduced into the convenient sites of hydrocortisone and prednisolone via the amidation or condensation reactions to form the corresponding linkers 7a-d, 8a-d, 9a,b, and 10a,b in acceptable yields. The bioassays such as prolongation of heterotopic transplanted cardiac tissue survival in vivo, inhibitory effects on phagocytosis of mouse peritoneal macrophages and concanavalin (ConA) or lipopolysaccharide (LPS) induced proliferation of mouse spleen lymphocytes in vitro show that at the comparable concentrations the immuno suppressive activities of the steroid-urotoxin linkers 7a-d, 8a-d, 9a,b, and 10a,b were higher than that of hydrocortisone, prednisolone, and the urotoxins alone, as well as significantly higher than that of the mixture of hydrocortisone and urotoxins or prednisolone and urotoxins. The so-called 'permissive action' may be responsible for the enhancement of the mentioned bioactivities of the steroid-urotoxin linkers 7a-d, 8a-d, 9a,b, and 10a,b. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.012
• 作为产物：
  描述：

  Boc-Asp(OH)-Gly-OBzl 、 苯甲醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到benzyl (3S)-4-{[2-(benzyloxy)-2-oxoethyl]amino}-3-[(tert-butoxycarbonyl)amino]-4-oxobutanoate
  参考文献：
  名称：

  Studies on peptides. CXXXII. Evaluation of two .BETA.-carboxyl protecting groups of aspartic acid, cycloheptyl and cyclooctyl, for peptide synthesis.

  摘要：

  对两种天冬氨酸β-酯（Asp(OR)，R=环庚基（Chp）和环辛基（Coc））的性质进行了研究。发现这两种保护基在三氟醋酸（0°C，2小时）下是稳定的，但在HF或1 M三氟甲烷磺酸-硫醚苯的三氟醋酸中（0°C，60分钟）会被切割。使用模型肽Z(OMe)-Ala-Asp(OR)-Gly-OBzl，研究了Asp(OR)残基在碱或酸中的行为。这些酯对于succinimide的形成比Bzl基在Et3N处理下的敏感度低。在酸去保护过程中，这些肽中succinimide的形成在两种情况下均低于7%。

  DOI：

  10.1248/cpb.34.864

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。
• Characterization of an acidic tripeptide in neurotoxic dialysate.
  作者：TAKASHI ABIKO、IKUKO ONODERA、HIROSHI SEKINO

  DOI：10.1248/cpb.28.1629

  日期：——

  An acidic tripeptide was isolated from neurotoxic dialysate by ultrafiltration with an Amicon Centriflo DM-5 membrane, followed by gel filtration on Sephadex G-15 and Sephadex G-10, and ion-exchange chromatography on DEAE-Sephadex A-25. The tripeptide thus obtained was identified as H-Glu-Asp-Gly-OH by amino acid analysis, Edman degradation, and measurement of physical constants and analytical data in comparison with those of the authentic tripeptide. This tripeptide inhibited LDH activity.

  通过Amicon Centriflo DM-5膜超滤，从神经毒性透析液中分离出一种酸性三肽，随后在Sephadex G-15和Sephadex G-10上进行凝胶过滤，并在DEAE-Sephadex A-25上进行离子交换色谱。通过氨基酸分析、EDMan降解以及物理常数和与真三肽的分析数据比较，确定所获得的三肽为H-Glu-Asp-Gly-OH。该三肽可抑制LDH活性。
• Rhodium(III)-Catalyzed C–H Alkenylation: Access to Maleimide-Decorated Tryptophan and Tryptophan-Containing Peptides
  作者：Jingjing Peng、Chunpu Li、Mirzadavlat Khamrakulov、Jiang Wang、Hong Liu

  DOI：10.1021/acs.orglett.0c00086

  日期：2020.2.21

  Maleimide is widely applied in many fields, especially in antibody-drug conjugations and peptide drugs. Herein, we develop a strategy for the C-H alkenylation of tryptophan and tryptophan-containing peptides, providing a synthetic route of decorating maleimide on peptides. The method has a high tolerance of functional groups and protecting groups. Furthermore, this method was applied to prepare peptide conjugation with molecules such as drugs and fluorescence probes. Moreover, macrocyclic peptides were obtained via this reaction.