Boc-L-Leu-OBt | 93957-20-1

• 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-L-Leu-OBt
• 英文别名: Boc-Leu-OBT；benzotriazol-1-yl (2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 93957-20-1
• 化学式: C₁₇H₂₄N₄O₄
• 分子量: 348.402
• InChiKey: UVKNRYZVRXVLJR-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-L-Leu-OBt 在 N-甲基吗啉 、 羟胺钾盐 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 tert-butyl 1-[4-hydroxy-2-(hydroxycarbamoyl)pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-ylcarbamate
  参考文献：
  名称：

  Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors

  摘要：

  A series of pyrrolidine derivatives were synthesized and evaluated for their ability to inhibit neuraminidase (NA) of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially 4-hydroXy-L-proline using a suitable synthetic strategy. These compounds showed potent inhibitory activity against influenza A neuraminidase. Within this series, five compounds, 6e, 9c, 9e, 9f, and 10e, have good potency (IC50 = 1.56-2.71 mu M) which are compared to that the NA inhibitor Oseltarnivir (IC50 = 1.06 mu M), and could be used as lead compoundS in the future. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.020
• 作为产物：
  描述：

  BOC-L-亮氨酸 、 1-羟基苯并三唑 以 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-L-Leu-OBt
  参考文献：
  名称：

  Application of an Automated Synthesis Suite to Parallel Solution-Phase Peptide Synthesis.

  摘要：

  使用一套自主研发的自动化合成系统，制备了72个四肽衍生物库，这些是用于合成具有药物吸引力的五肽的起始材料，采用了一种汇聚策略。首先，利用自动化合成工作站大规模（100-1000克）合成了18种二肽，然后使用自动化系统在中等规模（5-10克）合成了72种四肽。每个二肽或四肽均在单个操作周期中使用改良的甲磺酸方法制备，随后在小型规模（100毫克-1克）下利用机器人工作站并行合成了56种五肽的子库。

  DOI：

  10.1248/cpb.49.1147

文献信息

• Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method
  作者：Hironobu Hojo、Yuichi Murasawa、Hidekazu Katayama、Tsuyoshi Ohira、Yuko Nakahara、Yoshiaki Nakahara

  DOI：10.1039/b800884a

  日期：——

  Aryl thioesters of peptide segments were prepared by the conventional 9-fluorenylmethoxycarbonyl (Fmoc) strategy using a novel N-alkyl cysteine (NAC)-assisted thioesterification reaction. The peptide carrying NAC at its C-terminus was prepared by the Fmoc strategy and converted to the aryl thioester by 4-mercaptophenylacetic acid (MPAA) treatment without significant side reactions. The peptide thioester was used for the efficient preparation of 95-amino acid (AA) chemokine CCL27 by an Ag+-free thioester method.

  通过改进的N-烷基半胱氨酸(NAC)辅助硫酯化反应，采用传统的9-芴甲氧羰基(Fmoc)策略制备了肽段的芳基硫酯。含有C端NAC的肽段通过Fmoc策略制备，并通过4-巯基苯乙酸(MPAA)处理转化为芳基硫酯，过程中未发生显著的副反应。这种肽硫酯被用于高效制备95个氨基酸的趋化因子CCL27，采用无Ag+的硫酯方法。
• 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。
• Application of an Automated Synthesis Suite to Parallel Solution-Phase Peptide Synthesis.
  作者：Noritaka KURODA、Taeko HATTORI、Yoko FUJIOKA、David G. CORK、Chieko KITADA、Tohru SUGAWARA

  DOI：10.1248/cpb.49.1147

  日期：——

  An in-house developed automated synthesis suite was used to prepare a library of 72 tetrapeptide derivatives, the starting materials for pharmaceutically attractive pentapeptides, employing a convergent strategy. An initial set of 18 dipeptides were synthesized on a large-scale (100-1000 g) using automated synthesis workstations, and then 72 tetrapeptides were synthesized on a medium scale (5-10 g) using an automated system. Each di- or tetrapeptide was prepared in a single operating cycle using a modified methanesulfonic acid method, then a sub-library of 56 pentapeptides were synthesized in parallel, on a small-scale (100 mg-1 g) using a robotic workstation.

  使用一套自主研发的自动化合成系统，制备了72个四肽衍生物库，这些是用于合成具有药物吸引力的五肽的起始材料，采用了一种汇聚策略。首先，利用自动化合成工作站大规模（100-1000克）合成了18种二肽，然后使用自动化系统在中等规模（5-10克）合成了72种四肽。每个二肽或四肽均在单个操作周期中使用改良的甲磺酸方法制备，随后在小型规模（100毫克-1克）下利用机器人工作站并行合成了56种五肽的子库。
• β-Peptides: Synthesis by Arndt-Eistert homologation with concomitant peptide coupling. Structure determination by NMR and CD spectroscopy and by X-ray crystallography. Helical secondary structure of a β-hexapeptide in solution and its stability towards pe
  作者：Dieter Seebach、Mark Overhand、Florian N. M. Kühnle、Bruno Martinoni、Lukas Oberer、Ulrich Hommel、Hans Widmer

  DOI：10.1002/hlca.19960790402

  日期：1996.6.26

  The β-hexapeptide (H-β-HVal-β-HAla-β-HLeu)2-OH (2) was prepared from the component L-β-amino acids by conventional peptide synthesis, including fragment coupling. A cyclo-β-tri- and a cyclo-β-hexapeptide were also prepared. The β-amino acids were obtained from α-amino acids by Arndt-Eistert homologation. All reactions leading to the β-peptides occur smoothly and in high yields. The β-peptides were

  通过常规肽合成，包括片段偶联，由组分L-β-氨基酸制备β-六肽（H-β-HVal-β-HAla-β-HLeu）2 -OH（2）。还制备了环-β-三-和环-β-六肽。β-氨基酸是通过Arndt-Eistert同源从α-氨基酸获得的。导致β肽的所有反应均平稳且高产率地进行。β肽的特征在于其CD和NMR光谱（COSY，ROESY，TOCSY和NOE限制建模），以及X射线晶体结构分析。β-Sheet型结构（固态）和紧凑的左手或（M）3 1发现了5Å螺距的螺旋（在溶液中）。与α-肽的类似二级结构的比较显示出基本的差异，在这一点上最令人惊讶的是β-肽螺旋的更大的稳定性。β-肽与β-羟基链烷酸的低聚物之间存在结构关系，两类化合物之间的差异证明了氢键的作用。β-六肽2在37° C的H 2 O中在pH 2的胃蛋白酶中稳定裂解至少60小时，而相应的α-肽H-（Val-Ala-Leu）2 -OH在这些条件下瞬间裂解。情况。讨论了所描述结果的含义。
• (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.