3-tert-butoxycarbonylamino-2-tritylsulfanyl-propionic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-tert-butoxycarbonylamino-2-tritylsulfanyl-propionic acid
• 英文别名: N-Boc-S-Trt-isocysteine；Boc-iCys(Trt)-OH；3-[(2-Methylpropan-2-yl)oxycarbonylamino]-2-tritylsulfanylpropanoic acid
• 化学式: C₂₇H₂₉NO₄S
• 分子量: 463.598
• InChiKey: IGCJAKJCRBVBSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[1-[(2R,3S,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-fluorooxolan-2-yl]pyrazolo[3,4-d]pyrimidin-4-yl]-2-methylpropanamide 、 N-[4-(1-芘基)丁酰基]甘氨酸 、 N-[2-(3,4-二氢-5-甲基-2,4-二氧代-1(2H)-嘧啶基)乙酰基]-N-[2-[[(1,1-二甲基乙氧基)羰基]氨基]乙基]-甘氨酸 、 PNA-胞嘧啶单体 、 Fmoc-A(Bhoc)-aeg-OH 、 Fmoc-G(Bhoc)-aeg-OH 、 3-tert-butoxycarbonylamino-2-tritylsulfanyl-propionic acid 在 哌啶 、 N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 PYB-Lys(H-iCys-cctacag)-NH2
  参考文献：
  名称：

  核酸模板化反应：探针反应性和扩增信号和序列选择性读出策略的后果

  摘要：

  发出正确的信号：以DNA靶为催化剂的反应可以在DNA检测中放大信号。肽核酸（PNA）探针的反应性决定了给定的探针组是提供高灵敏度还是高选择性。仔细调整反应性，探针亲和力，并使用产物选择性读出方法，可以改善对DNA单碱基突变的灵敏分析，而几乎没有背景干扰。

  DOI：

  10.1002/chem.200900025
• 作为产物：
  描述：

  (2-oxo-1-oxa-4-thia-spiro[4.4]non-3-ylmethyl)-carbamic acid tert-butyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 3-tert-butoxycarbonylamino-2-tritylsulfanyl-propionic acid
  参考文献：
  名称：

  New isocysteine building blocks and chemoselective peptide ligation

  摘要：

  以硫代苹果酸为起点，通过简洁的三步法制备出 Boc、Fmoc 和 Cbz 保护的异半胱氨酸构筑模块。使用 Boc/Trt 保护的异半胱氨酸可以方便地获得异半胱氨酸肽，从而可以在水中对未受保护的肽片段进行化学选择性连接。比较了异半胱氨酸介导的连接与半胱氨酸介导的原生化学连接的 pH 依赖性。

  DOI：

  10.1039/b309235f

文献信息

• Single nucleotide specific detection of DNA by native chemical ligation of fluorescence labeled PNA-probes
  作者：Christian Dose、Oliver Seitz

  DOI：10.1016/j.bmc.2007.04.059

  日期：2008.1

  DNA-directed chemical ligations provide the opportunity to diagnose DNA sequences with very high sequence specificity. Fluorescent labels have been attached to reactive probes to enable the homogeneous detection of DNA and RNA. However, it has frequently been found that the attachment of fluorescent labels results in decreases of ligation fidelity. Herein we describe the development of a fluorogenic ligation reaction that provides for 10(2)-fold to perfect sequence selectivity. The reaction is based on the isocysteine-mediated native chemical PNA ligation. It is shown that DNA-induced rate accelerations of similar to 43.000-fold can be obtained through subtle variations of the ligation conditions. PNA-thioesters and isocysteine-PNA conjugates were labeled with FAM and TMR fluorophores, respectively. For gaining rapid synthetic access, a convenient on-resin labeling approach was developed. A new PNA monomer featuring an Alloc-protected lysine side chain was synthesized and coupled in solid-phase PNA synthesis. In the event of a ligation reaction the two fluorophores are brought into proximity. It is shown that fluorescence resonance energy transfer provides a positive fluorescence signal which is specific for product formation rather than for loss of starting materials. Single base mutations can be detected within minutes and with very high sequence selectivity at optimized conditions. (C) 2007 Elsevier Ltd. All rights reserved.
• US8921571B2
  申请人：——

  公开号：US8921571B2

  公开（公告）日：2014-12-30
• Nucleic Acid Templated Reactions: Consequences of Probe Reactivity and Readout Strategy for Amplified Signaling and Sequence Selectivity
  作者：Tom N. Grossmann、Oliver Seitz

  DOI：10.1002/chem.200900025

  日期：2009.7.6

  Making the right signals: Reactions in which the DNA target acts as a catalyst allow amplified signaling in the detection of DNA. The reactivity of the peptide nucleic acid (PNA) probes determines whether a given probe set provides high sensitivity or high selectivity. The careful adjustment of reactivity, probe affinity, and the use of a product‐selective readout method allows improvements in the

  发出正确的信号：以DNA靶为催化剂的反应可以在DNA检测中放大信号。肽核酸（PNA）探针的反应性决定了给定的探针组是提供高灵敏度还是高选择性。仔细调整反应性，探针亲和力，并使用产物选择性读出方法，可以改善对DNA单碱基突变的灵敏分析，而几乎没有背景干扰。
• New isocysteine building blocks and chemoselective peptide ligation
  作者：Christian Dose、Oliver Seitz

  DOI：10.1039/b309235f

  日期：——

  Boc-, Fmoc- and Cbz-protected isocysteine building blocks were prepared by a concise three-step procedure starting from thiomalic acid. The use of Boc/Trt-protected isocysteine provided convenient access to isocysteinyl peptides that allow the chemoselective ligation of unprotected peptide fragments in water. The pH-dependency of the isocysteine-mediated ligation was compared with that of cysteine-mediated native chemical ligation.

  以硫代苹果酸为起点，通过简洁的三步法制备出 Boc、Fmoc 和 Cbz 保护的异半胱氨酸构筑模块。使用 Boc/Trt 保护的异半胱氨酸可以方便地获得异半胱氨酸肽，从而可以在水中对未受保护的肽片段进行化学选择性连接。比较了异半胱氨酸介导的连接与半胱氨酸介导的原生化学连接的 pH 依赖性。