Boc-Glu(Bzl)-OBt | 104706-58-3

• 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-Glu(Bzl)-OBt
• 英文别名: 1-O-(benzotriazol-1-yl) 5-O-benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate
• CAS: 104706-58-3
• 化学式: C₂₃H₂₆N₄O₆
• 分子量: 454.483
• InChiKey: BIQCLZVNIOIQPN-SFHVURJKSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  121.64
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Boc-Glu(Bzl)-OBt 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 N-叔丁氧羰基-L-谷氨酸 1-甲酯
  参考文献：
  名称：

  Synthesis of cationic porphyrin modified amino acids

  摘要：

  在侧链上带有卟啉基团的氨基酸衍生物通过将卟啉与谷氨酸侧链偶联合成；这些化合物的实用性通过它们在固相合成带有阳离子卟啉的肽中的应用以及对其DNA结合性质的研究得以展示。

  DOI：

  10.1039/b508380j
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 1.25h， 生成 Boc-Glu(Bzl)-OBt
  参考文献：
  名称：

  Meldal, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 250 - 256

  摘要：

  DOI：

文献信息

• Synthesis of the octadecapeptide corresponding to positions 32 to 49 of the revised amino acid sequence of thymopoietin II and its effect on low E-rosette forming cells of an aged patient with chronic renal failure.
  作者：TAKASHI ABIKO、HIROSHI SEKINO

  DOI：10.1248/cpb.30.3271

  日期：——

  The octadecapeptide, H-Arg-Lys-Asp-Val-Tyr-Val-Glu-Leu-Tyr-Leu-Gln-Ser-Leu-Thr-Ala-Leu-Lys-Arg-OH, corresponding to positions 32 to 49 of the revised amino acid sequence of bovine thymopoietin II was synthesized by the azide condensation of three fragments, (32-36), (37-41) and (42-49), followed by deprotection with hydrogen fluoride in the presence of anisole-thioanisole-o-cresol. The in vitro addition of the synthetic thymopoietin II (32-49) significantly restored the low E-rosette forming capacity of cells from an aged patient with chronic renal failure to normal levels. The in vitro effect of [Gln38, Thr43, Val47]-thymopoietin II (32-49) on the low E-rosette forming capacity of cells from the aged patient with chronic renal failure was also compared with that of the synthetic thymopoietin II (32-49). The [Gln38, Thr43, Val47]-thymopoietin II (32-49) was approximately equipotent with the synthetic thymopoietin II (32-49) at a concentration of 100 μg/ml.

  十八肽H-Arg-Lys-Asp-Val-Tyr-Val-Glu-Leu-Tyr-Leu-Gln-Ser-Leu-Thr-Ala-Leu-Lys-Arg-OH，对应于牛胸腺生成素II修订后的氨基酸序列的第32至49位，通过三个片段(32-36)、(37-41)和(42-49)的叠氮化物缩合合成，随后在茴香硫醚-邻甲酚存在下用氢氟酸脱保护。体外添加合成的胸腺生成素II(32-49)显著恢复了来自慢性肾衰竭老年患者的细胞的低E玫瑰花形成能力至正常水平。[Gln38, Thr43, Val47]胸腺生成素II(32-49)对来自慢性肾衰竭老年患者的细胞的低E玫瑰花形成能力的影响也与合成的胸腺生成素II(32-49)进行了比较。在100 μg/ml的浓度下，[Gln38, Thr43, Val47]胸腺生成素II(32-49)与合成的胸腺生成素II(32-49)大致等效。
• A 12-Porphyrin System: Syntheses of Peptide Porphyrins with Multiple Histidines and the Aggregation Behavior in the Presence of Hemin
  作者：Masato Ushiyama、Atsushi Yoshino、Takeshi Yamamura、Yasuo Shida、Fumio Arisaka

  DOI：10.1246/bcsj.72.1351

  日期：1999.6

  We succeeded in combining multiple-histidine peptides with porphyrins; that is to say, we synthesized three peptide porphyrins consisting of α4-meso-tetrakis(o-aminophenyl)porphyrin, α4-H2TAPP, and amphiphilic peptide, α4-(PepA18)n(AG)4−n-H2TAPP (n = 1, 3, and 4; PepA18 = EEALEKHEKALEKHEKAG), in the liquid phase. These compounds were designed to construct multiple porphyrin systems; in other words, each peptide attached on the H2TAPP was designed to contain two histidines. The stability of the porphyrins, (AG)4-H2TAPP and (AG)1(Boc-AG)3-H2TAPP, as well as the coupling conditions between the porphyrin fragments and the 16-residue peptide, EEALEKHEKALEKHEK, to give α4-(PepA18)n(AG)4−n-H2TAPP (n = 1, 3, and 4) were studied in detail with respect to the temperature, solvents, coupling reagents, additives, and amines. This search revealed that the combination of DMF/benzotriazol-1-yl-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP)/N,N-diisopropylethylamine is suitable for the purpose. The search also clarified that it is possible to synthesize α4-(PepA18)4-H2TAPP and α4-(PepA18)3(AG)1-H2TAPP selectively by choosing the coupling additives 1-hydroxy-7-azabenzotriazole (HOAt) and 1-hydroxybenzotriazole (HOBt), respectively.All of the compounds showed 40% helicity in a solution (phospate buffer, pH = 7.0) containing 2,2,2-trifluoroethanol (TFE). The UV-vis and circular-dichroism spectrophotometric titrations of Fe(III) protoporphyrin IX chloride, B, with α4-(PepA18)4-ZnTAPP, A, indicated that up to three equivalents of B were incorporated into A in a buffer solution containing 15% TFE. Sedimentation-equilibrium ultracentrifugation experiments showed that A is a dimer in the solution, and that this dimer is transformed to a trimer when B is incorporated into A. These results suggest that A achieves a 12-porphyrin system consisting of different kinds of metalloporphyrin.

  我们成功地将多组氨酸肽与卟啉结合，即在液相中合成了三种由α4-均四(邻氨基苯基)卟啉、α4-H2TAPP和两亲性肽组成的肽卟啉，α4-(PepA18)n(AG)4−n-H2TAPP（n=1,3,4；PepA18=EEALEKHEKALEKHEKAG）。这些化合物旨在构建多卟啉体系；换言之，每个附着在H2TAPP上的肽段设计为含有两个组氨酸。针对温度、溶剂、偶联试剂、添加剂和胺，详细研究了卟啉的稳定性，(AG)4-H2TAPP和(AG)1(Boc-AG)3-H2TAPP，以及卟啉片段与16残基肽，EEALEKHEKALEKHEK之间的耦合条件，以生成α4-(PepA18)n(AG)4−n-H2TAPP（n=1,3,4）。研究发现，DMF/苯并三唑-1-基氧基三(吡咯烷基)磷鎓六氟磷酸盐(PyBOP)/N,N-二异丙基乙胺的组合适用于此目的。研究还阐明，通过选择偶联添加剂1-羟基-7-氮杂苯并三唑(HOAt)和1-羟基苯并三唑(HOBt)，可以有选择性地合成α4-(PepA18)4-H2TAPP和α4-(PepA18)3(AG)1-H2TAPP。所有化合物在含有2,2,2-三氟乙醇(TFE)的溶液(磷酸盐缓冲液，pH=7.0)中均显示出40%的螺旋度。Fe(III)原卟啉IX氯化物B与α4-(PepA18)4-ZnTAPP，A的紫外-可见光和圆二色光谱滴定表明，在含有15% TFE的缓冲溶液中，最多可掺入三个当量的B到A中。沉降平衡超速离心实验显示，A在溶液中为二聚体，当B掺入A时，该二聚体转变为三聚体。这些结果表明，A实现了由不同金属卟啉组成的12卟啉体系。
• Meldal, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 242 - 249
  作者：Meldal

  DOI：——

  日期：——
• Preparation of large macrocyclic peptides using the oxime resin
  作者：Jean-Philippe Blanchette、Patrick Ferland、Normand Voyer

  DOI：10.1016/j.tetlet.2007.05.033

  日期：2007.7

  We exploited a peptide cyclization-cleavage reaction on oxime resin (PCOR) to obtain in one key step large macrocyclic peptides. Herein, we report on the different parameters affecting the cyclization-oligomerization reaction, whether to favor cyclic monomer or cyclic oligomers formation. (c) 2007 Elsevier Ltd. All rights reserved.
• (3S)-N-(l-Aminoacyl)-1,2,3,4-tetrahydroisoquinolines, a class of novel antithrombotic agents: Synthesis, bioassay, 3D QSAR, and ADME analysis
  作者：Meiqing Zheng、Xiaoyi Zhang、Ming Zhao、Heng Wei Chang、Wei Wang、Yuji Wang、Shiqi Peng

  DOI：10.1016/j.bmc.2008.09.019

  日期：2008.11

  To increase antithrombotic activity, 3S-tetrahydroisoquinoline-3-carboxylic acid (1) was modified with natural amino acids to form 19 novel dipeptide analogs, 3S-tetrahydroisoquinoline-3-carboxyamino acids (5a-s), targeting the intestinal peptide transport system. In vitro assay of 5a-s indicated that their potencies for inhibiting adenosine diphosphate (ADP), arachidonic acid (AA), platelet-activating factor (PAF), and thrombin (TH)-induced platelet aggregations were higher than that of 1. Additionally, in vivo assay of 5a-s indicated that their potencies for inhibiting thrombogenesis in rats were also higher than that of 1. Among the candidates, 5h with Ser attachment showed the most impressive features for further development. According to molecular field analysis based Cerius(2) QSAR module, two equations (r, 0.961 and 0.988) correlating the structures with both in vitro and in vivo activities of 5a-s were established. ADMET calculations predict higher intestinal absorption for compounds 5a-s. Further investigation with 5h as a lead compound is underway. (C) 2008 Elsevier Ltd. All rights reserved.