N-Succinimidyl 4-<(tert-butyloxycarbonyl)amino>phenylacetate | 120059-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Succinimidyl 4-<(tert-butyloxycarbonyl)amino>phenylacetate
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]acetate
• CAS: 120059-12-3
• 化学式: C₁₇H₂₀N₂O₆
• 分子量: 348.356
• InChiKey: BBPRZXMDCQJZAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-Succinimidyl 4-<(tert-butyloxycarbonyl)amino>phenylacetate 在 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 [125I]-PAPA-XAC
  参考文献：
  名称：

  Electrophilic derivatives of purines as irreversible inhibitors of A1 adenosine receptors

  摘要：

  Functionalized congeners derived from 1,3-dipropyl-8-phenylxanthine and from N6-phenyladenosine were derivatized to contain electrophilic groups (isothiocyanate, N-hydroxysuccinimide ester, maleimide, sulfonyl chloride, or alpha-haloacyl group) capable of reaction with nucleophiles on biopolymers. The goal was to inhibit chemically the A1 adenosine receptor by using reactive agonist and antagonist ligands. Some of the electrophilic derivatives were synthesized through acylation of amine-functionalized congeners using hetero- or homobifunctional reagents available for protein cross-linking. The affinity for A1 adenosine receptors was evaluated in competitive binding assays by using rat and bovine brain membranes. Several xanthine and adenosine thiourea derivatives prepared from 1,3- and 1,4-phenylene diisothiocyanate (DITC) were potent irreversible inhibitors of adenosine receptors. Derivatives of m-DITC, at concentrations between 10 and 500 nM, irreversibly eliminated binding at 90% of the A1-receptor sites. Receptor affinity of both xanthine and adenosine derivatives containing distal phenylthiourea substituents was diminished by electron-donating groups on the ring.

  DOI：

  10.1021/jm00125a019
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 disodium hydrogenphosphate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-Succinimidyl 4-<(tert-butyloxycarbonyl)amino>phenylacetate
  参考文献：
  名称：

  Electrophilic derivatives of purines as irreversible inhibitors of A1 adenosine receptors

  摘要：

  Functionalized congeners derived from 1,3-dipropyl-8-phenylxanthine and from N6-phenyladenosine were derivatized to contain electrophilic groups (isothiocyanate, N-hydroxysuccinimide ester, maleimide, sulfonyl chloride, or alpha-haloacyl group) capable of reaction with nucleophiles on biopolymers. The goal was to inhibit chemically the A1 adenosine receptor by using reactive agonist and antagonist ligands. Some of the electrophilic derivatives were synthesized through acylation of amine-functionalized congeners using hetero- or homobifunctional reagents available for protein cross-linking. The affinity for A1 adenosine receptors was evaluated in competitive binding assays by using rat and bovine brain membranes. Several xanthine and adenosine thiourea derivatives prepared from 1,3- and 1,4-phenylene diisothiocyanate (DITC) were potent irreversible inhibitors of adenosine receptors. Derivatives of m-DITC, at concentrations between 10 and 500 nM, irreversibly eliminated binding at 90% of the A1-receptor sites. Receptor affinity of both xanthine and adenosine derivatives containing distal phenylthiourea substituents was diminished by electron-donating groups on the ring.

  DOI：

  10.1021/jm00125a019

文献信息

• Photoredox‐Catalyzed Labeling of Hydroxyindoles with Chemoselectivity (PhotoCLIC) for Site‐Specific Protein Bioconjugation
  作者：Soumya Jyoti Singha Roy、Conor Loynd、Delilah Jewel、Sarah E. Canarelli、Elise D. Ficaretta、Quan A. Pham、Eranthie Weerapana、Abhishek Chatterjee

  DOI：10.1002/anie.202300961

  日期：2023.7.3

  bioconjugation reaction, PhotoCLIC, has been developed for chemoselective attachment of aromatic amines onto a 5-hydroxytryptophan (5HTP) residue site-specifically preinstalled in a full-length protein using genetic code expansion technology. PhotoCLIC has a wide substrate scope and is compatible with the strain-promoted azide-alkyne cycloaddition to enable site-specific dual-labeling of target proteins.

  一种新型可见光催化生物共轭反应 PhotoCLIC 已被开发出来，用于使用遗传密码扩展技术将芳香胺化学选择性地附着到全长蛋白质中位点特异性预安装的 5-羟基色氨酸 (5HTP) 残基上。 PhotoCLIC 具有广泛的底物范围，并且与菌株促进的叠氮-炔环加成兼容，可实现目标蛋白的位点特异性双标记。
• [EN] A CHEMOSELECTIVE PHOTOCHEMICAL BIOCONJUGATION REACTION AND METHODS OF USE THEREOF<br/>[FR] RÉACTION DE BIOCONJUGAISON PHOTOCHIMIQUE CHIMIOSÉLECTIVE ET SES PROCÉDÉS D'UTILISATION
  申请人：TRUSTEES BOSTON COLLEGE

  公开号：WO2023205769A1

  公开（公告）日：2023-10-26

  Described herein is a visible light enabled photocatalytic oxidative protein bioconjugation reaction directed towards site-specifically incorporating non-canonical amino acids (ncAA).

  本文描述的是一种利用可见光的光催化氧化蛋白质生物共轭反应，该反应针对特定位点结合非典型氨基酸（ncAA）。
• JACOBSON, KENNETH A.;BARONE, SUZANNE;KAMMULA, UDAI;STILES, GARY L., J. MED. CHEM., 32,(1989) N, C. 1043-1051
  作者：JACOBSON, KENNETH A.、BARONE, SUZANNE、KAMMULA, UDAI、STILES, GARY L.

  DOI：——

  日期：——