(S)-2-Amino-3-{3,5-bis-[(bis-pyridin-2-ylmethyl-amino)-methyl]-4-hydroxy-phenyl}-propionic acid methyl ester | 909723-88-2

• 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: (S)-2-Amino-3-{3,5-bis-[(bis-pyridin-2-ylmethyl-amino)-methyl]-4-hydroxy-phenyl}-propionic acid methyl ester
• 英文别名: H-DpaTyr-OMe；methyl (2S)-2-amino-3-[3,5-bis[[bis(pyridin-2-ylmethyl)amino]methyl]-4-hydroxyphenyl]propanoate
• CAS: 909723-88-2
• 化学式: C₃₆H₃₉N₇O₃
• 分子量: 617.751
• InChiKey: UYWXFNYPDFXMSF-UMSFTDKQSA-N

物化性质

• 沸点：
  717.5±55.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-3-{3,5-bis-[(bis-pyridin-2-ylmethyl-amino)-methyl]-4-hydroxy-phenyl}-propionic acid methyl ester 以 乙醇 、 2,2,2-三氟乙醇 为溶剂， 反应 18.0h， 生成 methyl (2S)-2-[[2-(benzotriazol-1-ylmethylamino)-2-oxoethyl]-[6-(2,5-dioxopyrrol-1-yl)hexanoyl]amino]-3-[3,5-bis[[bis(pyridin-2-ylmethyl)amino]methyl]-4-hydroxyphenyl]propanoate
  参考文献：
  名称：

  POLY HETEROCYCLIC CONJUGATES AND THEIR PHARMACEUTICAL USES

  摘要：

  以下是化学式（I）的化合物以及含有其中一种化合物的药物组合物：这里定义了每个变量。还披露了一种使用化合物（I）治疗与细胞生长失控相关症状的方法。

  公开号：

  US20210403483A1
• 作为产物：
  描述：

  3-{3,5-bis[(bis-pyridin-2-ylmethyl-amino)methyl]-4-hydroxyphenyl}-2-(tert-butoxycarbonylamino)propionic acid methyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到(S)-2-Amino-3-{3,5-bis-[(bis-pyridin-2-ylmethyl-amino)-methyl]-4-hydroxy-phenyl}-propionic acid methyl ester
  参考文献：
  名称：

  Oligo-Asp Tag/Zn(II) 复合探针作为蛋白质标记和荧光成像的新对

  摘要：

  为了在复杂的生物系统中完成对特定蛋白质的选择性标记，需要掺入蛋白质中的肽标签和互补的小分子探针。尽管已经开发了多种肽标签/探针对作为蛋白质分析的分子工具，但适用于蛋白质实时成像的对的可用性仍然有限。我们现在报告了一个新的肽标签/人工探针对，由可遗传编码的低聚天冬氨酸序列（D4 标签，(D4)n，n = 1-3）和相应的多核 Zn(II) 复合物 (Zn(II)- DpaTyrs）。Zn(II)-DpaTyr 探针与 D4 标签的强结合亲和力是多重配位键和多价效应的结果。用等温滴定量热法定量测定。

  DOI：

  10.1021/ja0618604

文献信息

• Binuclear Ni^II-DpaTyr Complex as a High Affinity Probe for an Oligo-Aspartate Tag Tethered to Proteins
  作者：Akio Ojida、Sho-hei Fujishima、Kei Honda、Hiroshi Nonaka、Sho-hei Uchinomiya、Itaru Hamachi

  DOI：10.1002/asia.200900362

  日期：2010.4.1

  of a short‐peptide tag and a small molecular probe is a versatile molecular tool for protein detection, handling, and purification, and so forth. In this manuscript, we report that the binuclear NiII‐DpaTyr (DpaTyr=bis((dipicolylamino)methyl)tyrosine) complex serves as a strong binding probe for an oligo‐aspartate tag tethered to a protein. Among various binuclear metal complexes of M‐DpaTyr (M=ZnII

  短肽标签和小分子探针的互补识别对是用于蛋白质检测，处理和纯化等的多功能分子工具。在此手稿中，我们报道了双核Ni II -DpaTyr（DpaTyr =双（（二吡啶甲酰基氨基）甲基）酪氨酸）复合物可作为与蛋白质连接的低聚天冬氨酸标签的强结合探针。在M‐DpaTyr的各种双核金属络​​合物中（M = Zn II，Ni II，Mn II，Cu II，Cd II，Co III和Fe III），我们发现Ni II‐ DpaTyr（1-2 Ni2 +）显示出强结合亲和力（表观结合常数：ķ应用≈10 5 中号-1），用于寡聚天门冬氨酸的肽中性含水条件下（50米中号HEPES，百米中号NaCl，pH为7.2）。等温滴定热量法（ITC）的详细研究表明，三天冬氨酸D3标签（DDD）是1-2Ni2 +在1：1结合化学计量法中识别的最佳序列。另一方面，除Ni II-和Zn II -DpaTyr外，DpaTyr的其
• Ratiometric fluorescence detection of a tag fused protein using the dual-emission artificial molecular probe
  作者：Kei Honda、Eiji Nakata、Akio Ojida、Itaru Hamachi

  DOI：10.1039/b608684e

  日期：——

  We have successfully developed a ratiometric detection system for protein of interest using the complementary recognition pair of the tetra-aspartate peptide tag and the SNARF-appended Zn(II)–DpaTyr probe.

  我们利用四天冬氨酸肽标签和 SNARF 应用 Zn(II)-DpaTyr 探针的互补识别对，成功开发了一种相关蛋白质的比率检测系统。
• Non-enzymatic Covalent Protein Labeling Using a Reactive Tag
  作者：Hiroshi Nonaka、Shinya Tsukiji、Akio Ojida、Itaru Hamachi

  DOI：10.1021/ja074176d

  日期：2007.12.1

  We describe herein a new method for covalent labeling of proteins using a complementary recognition pair of peptide tag and synthetic molecular probe. The rapid and specific covalent labeling of a tag-fused protein was achieved by the reaction on the tag site with the probe through their selective molecular recognition. The advantages of this method involve the facile functional modification and the high labeling specificity of the tag-fused protein, which are demonstrated in the labeling experiments in various conditions even inside cells.
• Anion-Mediated Phase Transfer of Zinc(II)-Coordinated Tyrosine Derivatives
  作者：Hua Jiang、Edward J. O'Neil、Kristy M. DiVittorio、Bradley D. Smith

  DOI：10.1021/ol0510421

  日期：2005.7.1

  Tyrosine-derived Zn2+ coordination complexes and their fluorescent NBD conjugates are synthesized in a short, high-yielding procedure. The Zn2+ complexes are highly water soluble, but in the presence of sodium laurate they readily transfer into an octanol layer. Furthermore, the NBD-labeled bis-Zn2+ complex can partition into vesicle membranes containing anionic phospholipids.
• Specific Enrichment of Phosphoproteins Using Functionalized Multivalent Nanoparticles
  作者：Leekyoung Hwang、Serife Ayaz-Guner、Zachery R. Gregorich、Wenxuan Cai、Santosh G. Valeja、Song Jin、Ying Ge

  DOI：10.1021/ja511833y

  日期：2015.2.25

  Analysis of protein phosphorylation remains a significant challenge due to the low abundance of phosphoproteins and the low stoichiometry of phosphorylation, which requires effective enrichment of phosphoproteins. Here we have developed superparamagnetic nanoparticles (NPs) whose surface is functionalized by multivalent ligand molecules that specifically bind to the phosphate groups on any phosphoproteins. These NPs enrich phosphoproteins from complex cell and tissue lysates with high specificity as confirmed by SDS-PAGE analysis with a phosphoprotein-specific stain and mass spectrometry analysis of the enriched phosphoproteins. This method enables universal and effective capture, enrichment, and detection of intact phosphoproteins toward a comprehensive analysis of the phosphoproteome.