(3S)-4-[(2,5-二氧代-1-吡咯烷基)氧基]-4-氧代-3-[[(苯基甲氧基)羰基]氨基]-丁酸苄酯 | 61464-33-3

• 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
• 中文名称: (3S)-4-[(2,5-二氧代-1-吡咯烷基)氧基]-4-氧代-3-[[(苯基甲氧基)羰基]氨基]-丁酸苄酯
• 中文别名: (3S)-丁酸4-[(2,5-二氧代-1-吡咯烷基)氧基]-4-氧代-3-[[(苯基甲氧基)羰基]氨基]-,苯甲酯
• 英文名称: N-carbobenzoxy-L-aspartic acid α-N-succinimidyl β-benzyl diester
• 英文别名: O^γ-benzyl-N^α-benzyloxycarbonylaspartic acid succinimidyl ester；Cbz-Asp(OBn)OSu；Z-aspartic acid β-benzyl ester succinimidyl ester；Z-Asp(OBzl)-OSu；4-O-benzyl 1-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-(phenylmethoxycarbonylamino)butanedioate
• CAS: 61464-33-3
• 化学式: C₂₃H₂₂N₂O₈
• 分子量: 454.436
• InChiKey: WCIMRCGAANBKFS-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

安全信息

• 储存条件：
  室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  (3S)-4-[(2,5-二氧代-1-吡咯烷基)氧基]-4-氧代-3-[[(苯基甲氧基)羰基]氨基]-丁酸苄酯 在 N-羟基-5-降冰片烯-2,3-二甲酰亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 N-CBZ-β-benzyl-L-aspartyl-D-alanine (R,S)-α-tert-butylbenzylamide
  参考文献：
  名称：

  Discovery and Synthesis of a New Series of High-Potency L-Aspartyl-D-.alpha.-aminoalkanoyl-(S)-.alpha.-alkylbenzylamide Sweeteners

  摘要：

  A new series of L-aspartyl-D-amino acid amide sweeteners is described in which the amide portion is prepared from an cl-alkyl-substituted benzylamine. These materials show good taste characteristics and are 5 times more stable than aspartame at typical beverage pH (3-4). The most potent member of the series is L-aspartyl-D-alpha-aminobutyric acid (S)-alpha-ethylbenzylamide, having a sweetness potency 2000 times that of a 10% sucrose solution.

  DOI：

  10.1021/jf00056a003
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 CBZ-L-天门冬氨酸β-苄酯 在 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 以69.7%的产率得到(3S)-4-[(2,5-二氧代-1-吡咯烷基)氧基]-4-氧代-3-[[(苯基甲氧基)羰基]氨基]-丁酸苄酯
  参考文献：
  名称：

  天冬氨酰三肽酯的构味关系

  摘要：

  已经合成了与甜肽的结构特征相关的一系列 24 种 L-α-Asp-Gly-Gly-OMe 类似物。二肽的结构-味道关系的规则在于甜天冬氨酰三肽酯。为了使天冬氨酰三肽酯具有甜味，第二个氨基酸必须具有 D 构型，并且在 R2 处有一个小的、紧凑的烷基（Me、Et 或 i-Pr）。强烈的甜味需要第三个氨基酸的 L 构型。已经得出结论，R2 处的小烷基通过疏水相互作用参与与受体的结合并增加甜味效力。

  DOI：

  10.1246/bcsj.57.3197

文献信息

• Synthesis and Biological Activity of a Novel Class of Small Molecular Weight Peptidomimetic Competitive Inhibitors of Protein Tyrosine Phosphatase 1B
  作者：Scott D. Larsen、Tjeerd Barf、Charlotta Liljebris、Paul D. May、Derek Ogg、Theresa J. O'Sullivan、Barbara J. Palazuk、Heinrich J. Schostarez、F. Craig Stevens、John E. Bleasdale

  DOI：10.1021/jm010393s

  日期：2002.1.1

  sulfate with other potential phosphate mimics. The most potent analogue arising from this effort was triacid 71, which inhibits PTP1B competitively with a K(i) = 0.22 microM without inhibiting SHP-2 or LAR at concentrations up to 100 microM. Overall, the inhibitors generated in this work showed little or no enhancement of insulin signaling in cellular assays. However, potential prodrug triester 70 did induce

  蛋白质酪氨酸磷酸酶1B（PTP1B）部分地通过使胰岛素受体（IR）的β亚基调节域内的关键酪氨酸残基去磷酸化，从而负调节胰岛素信号传导，从而减弱受体酪氨酸激酶的活性。因此，抑制PTP1B有望改善胰岛素抵抗，并且最近已成为旨在鉴定用于治疗II型糖尿病的新药物的发现工作的重点。我们以前曾报道三肽Ac-Asp-Tyr（SO（3）H）-Nle-NH（2）是PTP1B的令人惊讶的有效抑制剂（K（i）= 5 microM）。为了改善该引线的稳定性和效力以及减弱其肽特性，进行了模拟程序。该程序初始阶段的具体内容包括用非氨基酸成分替换N和C末端，修饰酪氨酸亚基以及用其他潜在的磷酸盐模拟物替换硫酸酪氨酸。从这种努力中产生的最有效的类似物是三酸71，它以K（i）= 0.22 microM竞争性抑制PTP1B，而在浓度高达100 microM的情况下却不抑制SHP-2或LAR。总体而言，这项工作中产生的抑制剂在细
• Process for the preparation of carboxylic acid succinimidyl esters
  申请人：DSM Chemie Linz GmbH

  公开号：US05734064A1

  公开（公告）日：1998-03-31

  A process for the preparation of carboxylic acid succinimidyl esters by reaction of N-hydroxysuccinimide with a carboxylic acid and a halophosphoric acid ester of the formula ##STR1## is desired, in which R.sub.1 and R.sub.2 are identical or different and are a C.sub.2 - to C.sub.6 -alkyl radical or a phenyl radical, or R.sub.1 and R.sub.2 The process is carried out in the presence of a base in a diluent at a temperature of 0.degree. C. up to 100.degree. C. with isolation of the corresponding carboxylic acid succinimidyl ester.

  一种通过N-羟基琥珀酰亚胺与羧酸和具有公式##STR1##的卤代磷酸酯反应制备羧酸琥珀酰亚胺酯的方法，其中R.sub.1和R.sub.2相同或不同，是C.sub.2-C.sub.6-烷基基团或苯基团，或R.sub.1和R.sub.2在稀释剂中在0°C至100°C的温度下在碱的存在下进行，隔离相应的羧酸琥珀酰亚胺酯。
• Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA
  作者：S. De、E. Groaz、L. Margamuljana、M. Abramov、P. Marlière、P. Herdewijn

  DOI：10.1039/c5ob00157a

  日期：——

  The incorporation and extension of synthetically unprecedented nucleoside phosphoramidate sulfonates is demonstrated using thermophilic and mesophilic microbial polymerases.

  使用嗜热和中温微生物聚合酶展示了合成前所未有的核苷酸磷酸酰胺磺酸盐的合并和扩展。
• Structure–Taste Relationships of Aspartyl Tetrapeptide Esters
  作者：Yasuo Ariyoshi

  DOI：10.1246/bcsj.58.1727

  日期：1985.6

  A series of fourteen analogues of l-α-Asp–Gly–Gly–Gly–OMe has been synthesized in relation to structural features of sweet peptides. The rule in the structure-taste relationships of tripeptides barely applies to the aspartyl tetrapeptide esters. In order for the aspartyl tetrapeptide esters to be sweet, the second amino acid must have a d-configuration and a small, compact alkyl side chain. However, the sweetness was accompanied by a bitter or astringent taste. Moreover, some of the tetrapeptides were not sweet but bitter, though they satisfied the requirements for sweet peptides. With increasing length of a peptide, it becomes difficult to fit the deep receptor pocket.

  已合成一系列十四种l-α-Asp–Gly–Gly–Gly–OMe的类似物，与甜味肽的结构特征相关。三肽的结构-味道关系规则几乎不适用于天冬氨酰四肽酯。为了让天冬氨酰四肽酯具有甜味，第二个氨基酸必须具有d构型和一个小而紧凑的烷基侧链。然而，甜味伴随着苦味或涩味。此外，一些四肽不甜而是苦的，尽管它们符合甜味肽的要求。随着肽链长度的增加，很难适应深接收口袋。
• Study on the Structure Activity Relationships of NPTX-594, a Spider Toxin Belonging to the Type-B Acylpolyamine Structure
  作者：Tateaki Wakamiya、Tomohiko Kinoshita、Yoshihide Hattori、Yoshihiro Yamaguchi、Hideo Naoki、Gerardo Corzo、Terumi Nakajima

  DOI：10.1246/bcsj.77.331

  日期：2004.2

  In order to elucidate the structure activity relationships of the spider toxin termed NPTX-594, eleven toxin analogs were designed and synthesized, and their paralytic activities against cricket we...

  为了阐明被称为 NPTX-594 的蜘蛛毒素的构效关系，设计并合成了 11 种毒素类似物，以及它们对蟋蟀的麻痹活性...