N-tert-butyloxycarbonyl-O-tert-butyltyrosine N-hydroxysuccinimide ester | 30845-24-0

• 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: N-tert-butyloxycarbonyl-O-tert-butyltyrosine N-hydroxysuccinimide ester
• 英文别名: tert-butyloxycarbonyl-O-tert-butyltyrosine N-hydroxysuccinimide ester；Boc-Tyr(tBu)-Osu；Boc-Tyr(OtBu)-ONSu；Boc-Tyr(tBu)-OSu；(2,5-dioxopyrrolidin-1-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoate
• CAS: 30845-24-0
• 化学式: C₂₂H₃₀N₂O₇
• 分子量: 434.489
• InChiKey: MQQOVKSHQZBGCW-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  111.24
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-O-tert-butyltyrosine N-hydroxysuccinimide ester 在 N-乙基哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 lactam of tyrosyl-isoleucyl-isoleucyl-asparaginyl-S-(γ-carboxypropyl)cysteinyl-prolyl-leucyl-glycinamide
  参考文献：
  名称：

  Analogues of deamino-1-carba-oxytocin with an aliphatic amino acid in position 4: chemical synthesis and biological activities

  摘要：

  线性八肽通过溶液中的逐步合成制备。通过活性酯的方法进行环化，得到了缺氨基-1-卡巴-催产素的类似物，其中第4位的谷氨酰胺残基被异亮氨酸、亮氨酸或缬氨酸替代。测定了这些类似物的基本药理活性；它们的利尿作用低于催产素。

  DOI：

  10.1135/cccc19802714
• 作为产物：
  描述：

  O-叔丁基-L-酪氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 10.33h， 生成 N-tert-butyloxycarbonyl-O-tert-butyltyrosine N-hydroxysuccinimide ester
  参考文献：
  名称：

  Highly Selective Fluorogenic Multianalyte Biosensors Constructed via Enzyme-Catalyzed Coupling and Aggregation-Induced Emission

  摘要：

  The development of a highly selective and fast responsive fluorogenic biosensor for diverse analytes ranging from bioactive small molecules to specific antigens is highly desirable but remains a considerable challenge. We herein propose a new approach by integrating substrate-selective enzymatic reactions with fluorogens exhibiting aggregation-induced emission feature. Tyrosine-functionalized tetraphenylethene, TPE-Tyr, molecularly dissolves in aqueous media with negligible fluorescence emission; upon addition of horseradish peroxidase (HRP) and H2O2, effective cross-linking occurs due to HRP-catalyzed oxidative coupling of tyrosine moieties in TPE-Tyr. This leads to fluorescence emission turn-on and fast detection of H2O2 with high sensitivity and selectivity. As a validation of the new strategy's generality, we further configure it into the biosensor design for glucose through cascade enzymatic reactions and for pathologically relevant antigens (e.g., human carcinoembryonic antigen) by combining with the ELISA kit.

  DOI：

  10.1021/ja505278w

文献信息

• Functional profiling of adenylation domains in nonribosomal peptide synthetases by competitive activity-based protein profiling
  作者：Shota Kasai、Sho Konno、Fumihiro Ishikawa、Hideaki Kakeya

  DOI：10.1039/c5cc04953a

  日期：——

  Using a library of sulfamoyloxy-linked aminoacyl-AMP analogs, we describe competitive activity-based protein profiling to facilitate directly the functional prediction and assessment of adenylation domains in nonribosomal peptide synthetases in proteomic environments.

  利用磺胺氧基连接的氨酰-AMP类似物库，我们描述了竞争性活性蛋白质分析技术，以直接促进在蛋白质组学环境中对非核糖体肽合成酶中腺苷化结构域的功能预测和评估。
• Synthesis and properties of carba-6-analogues of oxytocin containing a deaminopenicillamine residue in position 1
  作者：Michal Lebl、Tomislav Barth、Linda Servítová、Jiřina Slaninová、Pavel Hrbas

  DOI：10.1135/cccc19842012

  日期：——

  A study was made of the influence of the so-called carba substitution of the disulphide bridge on the properties of inhibitors obtained by the introduction of deaminopenicillamine into position 1 of the oxytocin molecule. Two analogues - [dPen¹]carba-6-oxytocin (Ia) and [dPen¹, Tyr(Me)²]carba-6-oxytocin (Ib) were prepared and their biological activities were assayed. Compound Ia is a strong agonist in the uterotonic assay in vivo (280 I.U./mg) and a weak antagonistin the pressor assay. Compound Ib inhibited the utertonic activity of oxytocin in vitro (pA₂ = 8.43) and in vivo (pA₂ = 7.13) as well as the pressor action of lysine vasopressin (pA₂ = 7.43).

  一项研究探讨了所谓的卡巴取代二硫键对通过在催产素分子的位置1引入去氨基青霉胺而获得的抑制剂性质的影响。制备了两个类似物-[dPen¹]carba-6-催产素（Ia）和[dPen¹, Tyr(Me)²]carba-6-催产素（Ib），并对它们的生物活性进行了测定。化合物Ia在子宫收缩试验中是强激动剂（280 I.U./mg），在压力试验中是弱拮抗剂。化合物Ib抑制了催产素的子宫活性（体外pA₂ = 8.43，体内pA₂ = 7.13）以及赖氨酸加压素的升压作用（pA₂ = 7.43）。