Boc-εAhx-εAhx-OMe | 101817-20-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Boc-εAhx-εAhx-OMe
• 英文别名: Methyl 6-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoylamino]hexanoate
• CAS: 101817-20-3
• 化学式: C₁₈H₃₄N₂O₅
• 分子量: 358.478
• InChiKey: PDAJOWCQGZVWDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-εAhx-εAhx-OMe 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 H-EACA-EACA-OMe*HCl
  参考文献：
  名称：

  Paruszewski, Ryszard; Matusiak, Roza; Rostafinska-Suchar, Grazyna, Polish Journal of Chemistry, 1991, vol. 65, # 2-3, p. 361 - 368

  摘要：

  DOI：
• 作为产物：
  描述：

  叔丁氧羰酰基6-氨基己酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 11.5h， 生成 Boc-εAhx-εAhx-OMe
  参考文献：
  名称：

  Synthesis and Evaluation of a Photoactive Probe with a Multivalent Carbohydrate for Capturing Carbohydrate–Lectin Interactions

  摘要：

  Lectins are ubiquitous carbohydrate-binding proteins of nonimmune origin that are characterized by their specific recognition of defined monosaccharide or oligosaccharide structures. However, the use of carbohydrates to study lectin has been restricted by the weak binding affinity and noncovalent character of the interaction between carbohydrates and lectin. In this report, we designed and synthesized a multifunctional photoaffinity reagent composed of a trialkyne chain, a masked latent amine group, and a photoreactive 3-trifluoromethyl-3phenyl-diazirine group in high overall yield. Two well-defined chemistries, Huisgen-Sharpless click chemistry and amide bond coupling, were the key steps for installing the multivalent character and tag in our designed photoaffinity probe. The photolabeling results demonstrated that the designed probe selectively labeled the target lectin, RCA(120) (Ricinus communis Agglutinin), in an E. coli lysate and an asialoglycoprotein receptor (ASGP-R) on intact HepG2 cell membranes. Moreover, the probe also enabled the detection of weak protein protein interactions between RCA(120) and ovalbumin (OVA).

  DOI：

  10.1021/bc400306g

文献信息

• Proteasome selectivity towards Michael acceptor containing oligopeptide-based inhibitors
  作者：Wouter A. van der Linden、Paul P. Geurink、Chris Oskam、Gijsbert A. van der Marel、Bogdan I. Florea、Herman S. Overkleeft

  DOI：10.1039/b924134e

  日期：——

  The synthesis and biological evaluation of ten Michael acceptors containing potential proteasome inhibitors are described. Cellular targets of azide containing inhibitors Ib and VIIIb were assessed in HEK293T and RAW264.7 cells by a two step labeling strategy, followed by biotin-pulldown, affinity purification, on-bead tryptic digestion and LC-MS2 identification. This strategy appears to be an attractive alternative to gel-based competition assays.

  描述了含有潜在蛋白酶体抑制剂的十个迈克尔受体的合成与生物学评价。通过两步标记策略在HEK293T和RAW264.7细胞中评估了含有叠氮基抑制剂Ib和VIIIb的细胞内靶点，随后进行生物素-牵拉、亲和纯化、在珠上胰蛋白酶消化和LC-MS2鉴定。该策略似乎是一个有吸引力的乳胶凝胶竞争性测定的替代方案。
• Dimerized Linear Mimics of a Natural Cyclopeptide (TMC-95A) Are Potent Noncovalent Inhibitors of the Eukaryotic 20S Proteasome
  作者：Audrey Desvergne、Emilie Genin、Xavier Maréchal、Nerea Gallastegui、Laure Dufau、Nicolas Richy、Michael Groll、Joëlle Vidal、Michèle Reboud-Ravaux

  DOI：10.1021/jm4002007

  日期：2013.4.25

  Noncovalent proteasome inhibitors introduce an alternative mechanism of inhibition to that of covalent inhibitors used in cancer therapy. Starting from a noncovalent linear mimic of TMC-95A, a series of dimerized inhibitors using polyaminohexanoic acid spacers has been designed and optimized to target simultaneously two of the six active sites of the eukaryotic 20S proteasome. The homodimerized compounds

  与癌症治疗中使用的共价抑制剂相比，非共价蛋白酶体抑制剂引入了另一种抑制机制。从TMC-95A的非共价线性模拟开始，已设计并优化了一系列使用聚氨基己酸间隔基的二聚化抑制剂，以同时靶向真核20S蛋白酶体的六个活性位点中的两个。均二聚的化合物可有效抑制胰凝乳蛋白酶样（K i= 6-11 nM）和类胰蛋白酶的活性，而后酸活性的修饰较差。通过与酵母20S蛋白酶体复合的抑制剂的X射线晶体学确定非共价结合模式。评价了对人细胞中蛋白酶体活性的抑制。多价抑制剂概念的使用产生了高效且选择性的非共价化合物（不抑制钙蛋白酶和组织蛋白酶），与共价结合剂如硼替佐米和卡非佐米相比具有潜在的治疗优势。
• Probing the proteasome cavity in three steps: bio-orthogonal photo-reactive suicide substrates
  作者：Paul P. Geurink、Bogdan I. Florea、Gijs A. Van der Marel、Benedikt M. Kessler、Herman S. Overkleeft

  DOI：10.1039/c0cc03322g

  日期：——

  Tri-functional activity-based protein probes that encompass an electrophilic trap, a photo-reactive group and a bio-orthogonal ligation handle are described. With these, and in a three-step chemical proteomics approach, proteasomal catalytic sites are covalently and irreversibly modified, followed by photocrosslinking of these to flanking subunits and Staudinger–Bertozzi ligation for visualization and identification of the resulting conjugates.

  描述了基于三功能活性的蛋白质探针，其包含亲电陷阱、光反应基团和生物正交连接手柄。通过这些，在三步化学蛋白质组学方法中，蛋白酶体催化位点被共价和不可逆地修饰，然后将它们光交联到侧翼亚基上，并进行施陶丁格-贝尔托齐连接，以可视化和鉴定所得缀合物。
• Investigating a Boronate‐Affinity‐Guided Acylation Reaction for Labelling Native Antibodies
  作者：Avijit K. Adak、Kuan‐Ting Huang、Chien‐Yu Liao、Yuan‐Jung Lee、Wen‐Hua Kuo、Yi‐Ren Huo、Pei‐Jhen Li、Yi‐Ju Chen、Bo‐Shiun Chen、Yu‐Ju Chen、Kuo Chu Hwang、Wun‐Shang Wayne Chang、Chun‐Cheng Lin

  DOI：10.1002/chem.202104178

  日期：2022.3.22

  Adding function: A boronate-affinity ligand and an S-aryl thioester have been developed that are capable of labelling native Abs with a functional molecule. Additionally, a photoactivatable crosslinker allows purification of labelled Abs in a reagentless manner, thereby producing homogeneous Ab-drug conjugates.

  添加功能：已开发出一种硼酸盐亲和配体和 S-芳基硫酯，它们能够用功能性分子标记天然 Abs。此外，可光活化交联剂允许以无试剂方式纯化标记的 Abs，从而产生均质的 Ab-药物偶联物。
• Paruszewski, Ryszard; Matusiak, Roza; Rostafinska-Suchar, Grazyna, Polish Journal of Chemistry, 1989, vol. 63, # 4-12, p. 661 - 668
  作者：Paruszewski, Ryszard、Matusiak, Roza、Rostafinska-Suchar, Grazyna、Gumulka, Stanislaw、Misterek, Krystyna、Dorociak, Anna

  DOI：——

  日期：——