(N-tritylaminooxy)acetic acid | 112257-05-3

• 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: (N-tritylaminooxy)acetic acid
• 英文别名: 2-(Tritylamino)oxyacetic acid
• CAS: 112257-05-3
• 化学式: C₂₁H₁₉NO₃
• 分子量: 333.387
• InChiKey: CYNCHYUHEQCZSM-UHFFFAOYSA-N

物化性质

• 沸点：
  516.7±60.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (N-tritylaminooxy)acetic acid 在 copper(I) bromide dimethylsulfide complex 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 31.0h， 生成 N,N,N-trimethyl-2-oxo-2-((4-(4-((2-((tritylamino)oxy)acetamido)methyl)-1H-1,2,3-triazole1-yl)phenyl)amino)ethanaminium chloride
  参考文献：
  名称：

  REAGENT FOR MASS SPECTROMETRY

  摘要：

  本发明涉及适用于质谱测定分析物分子（如碳水化合物）以及该类试剂和分析物分子的加合物的试剂，并涉及所述试剂和加合物的应用。此外，本发明涉及用于质谱测定分析物分子的方法。

  公开号：

  US20200041470A1
• 作为产物：
  描述：

  三苯基氯甲烷 、 羧甲基羟胺半盐酸盐 在 三乙胺 作用下， 以 吡啶 为溶剂， 反应 22.0h， 以74%的产率得到(N-tritylaminooxy)acetic acid
  参考文献：
  名称：

  Construction of Highly Reactive Probes for Abasic Site Detection by Introduction of an Aromatic and a Guanidine Residue into an Aminooxy Group

  摘要：

  Abasic sites (AP sites) arise from hydrolysis of glycosidic bonds of DNA that is damaged by various external and internal processes; unrepaired AP sites give rise to genetic mutations. We have constructed highly reactive AID, site-detecting probes by introducing a hydrophobic and a hydrophilic residue in an aminooxy group. Synthesized probes containing either a naphthalene or a guanidine residue conjugate effectively with AP sites. In particular, a probe containing both functional groups shows the highest reaction rate, indicating that the hydrophobic and hydrophilic interactions act cooperatively in reaction with AP sites. The guanidine residue also contributes to the solubility of the molecules in aqueous media. The biotinylated probes provide much more sensitive detection of AP sites in genomic DNA than the conventional aldehyde-reactive probe.

  DOI：

  10.1021/ja904767k

文献信息

• Analogues of oxytocin with an oxime bridge using chemoselectively addressable building blocks
  作者：Franck Wahl、Manfred Mutter

  DOI：10.1016/0040-4039(96)01537-7

  日期：1996.9

  The synthesis of two novel amino-acid building blocks for the chemoselective ligation of unprotected peptides via oxime bond formation and their application in the solid phase peptide synthesis of oxytocin analogues with the disulfide altered to an oxime bridge are described.

  描述了两个新的氨基酸结构单元的合成，该结构单元用于通过肟键的化学键连接未保护肽的化学选择性连接以及它们在催产素类似物的固相肽合成中的应用，其中二硫键已转变为肟桥。
• Interstrand cross-link of DNA by covalently linking a pair of abasic sites
  作者：Kohei Ichikawa、Naoshi Kojima、Yu Hirano、Toshie Takebayashi、Keiko Kowata、Yasuo Komatsu

  DOI：10.1039/c2cc16785a

  日期：——

  A pair of apurinic/apyrimidinic sites formed in DNA has been covalently connected with bis(aminooxy) derivatives. The efficacy of the interstrand cross-link is associated with the structural tethering of two aminooxy groups. The interstrand cross-link constructed stable DNA scaffolds for enzyme alignment.

  DNA 中形成的一对嘌呤/近嘧啶位点与双（氨基氧基）衍生物进行了共价连接。链间交联的功效与两个氨基氧基的结构系链有关。链间交联为酶配位构建了稳定的 DNA 支架。
• Selective Labeling Aldehydes in DNA
  作者：Chaoxing Liu、Xiaomeng Luo、Yuqi Chen、Fan Wu、Wei Yang、Yafen Wang、Xiong Zhang、Guangrong Zou、Xiang Zhou

  DOI：10.1021/acs.analchem.8b04822

  日期：2018.12.18

  synthesized to selectively label the whole natural aldehydes present in DNAs including 5-formylcytosine, 5-formyluracil, and abasic sites. The fluorescence characteristics of the generated nucleosides have been examined in detail, and the reaction activities of hydroxylamine, amine groups toward aldehydes in DNA have been discussed with others, which will be a vital reference for designing chemicals for selective

  已经设计并合成了萘二甲酰亚胺羟胺探针，以选择性标记存在于DNA中的整个天然醛，包括5-甲酰基胞嘧啶，5-甲酰基尿嘧啶和脱碱基位点。详细检查了生成的核苷的荧光特性，并与其他人讨论了羟胺，胺基对DNA中的醛的反应活性，这对于设计用于DNA选择性标记的化学试剂将是至关重要的参考。
• Solid phase oxime ligations for the iterative synthesis of polypeptide conjugates
  作者：Isidore E. Decostaire、Dominique Lelièvre、Vincent Aucagne、Agnès F. Delmas

  DOI：10.1039/c4ob00760c

  日期：——

  couplings, which leads to loss of material. An efficient alternative is solid phase chemical ligation (SPCL) initially developed for native chemical ligation. We report here an extension of this approach to iterative oxime ligation reactions, and describe a streamlined approach for the modular preparation of oxime-containing polypeptides. In particular, we determined optimal conditions to remove the Aloc

  现在，通过顺序连接未保护的肽段，可以最佳地组装基于肽的复杂生物大分子。然而，该方法仍然受到多次连续的化学选择性偶联所需的费力的色谱纯化和处理步骤的限制，这导致材料的损失。一种有效的替代方法是最初为天然化学连接开发的固相化学连接（SPCL）。我们在这里报告此方法扩展到迭代肟连接反应，并描述了一种简化的方法，用于模块化制备含肟的多肽。特别是，我们确定了在存在氨基氧基和肟醚基的情况下去除Aloc基团的最佳条件，并且我们仅使用固体支持的化学转化方法，通过简化对C末端嫁接的未保护肽段的访问，扩展了C-N重复SPCL的适用性。含有肟的粗多肽的高纯度突出了我们方法的效率。
• 5-Formyl- and 5-Carboxydeoxycytidines Do Not Cause Accumulation of Harmful Repair Intermediates in Stem Cells
  作者：René Rahimoff、Olesea Kosmatchev、Angie Kirchner、Toni Pfaffeneder、Fabio Spada、Victor Brantl、Markus Müller、Thomas Carell

  DOI：10.1021/jacs.7b04131

  日期：2017.8.2

  5-Formyl-dC (fdC) and 5-carboxy-dC (cadC) are newly discovered bases in the mammalian genome that are supposed to be substrates for base excision repair (BER) in the framework of active demethylation. The bases are recognized by the monofunctional thymine DNA glycosylase (Tdg), which cleaves the glycosidic bond of the bases to give potentially harmful abasic sites (AP-sites). Because of the turnover of fdC and cadC during cell state transitions, it is an open question to what extent such harmful AP-sites may accumulate during these processes. Here, we report the development of a new reagent that in combination with mass spectrometry (MS) allows us to quantify the levels of AP-sites. This combination also allowed the quantification of beta-elimination (beta E) products, which are repair intermediates of bifunctional DNA glycosylases. In combination with feeding of isotopically labeled nucleosides, we were able to trace the intermediates back to their original nucleobases. We show that, while the steady-state levels of fdC and cadC are substantially increased in Tdg-deficient cells, those of both AP- and beta E-sites are unaltered. The levels of the detected BER intermediates are 1 and 2 orders of magnitude lower than those of cadC and fdC, respectively. Thus, neither the presence of fdC nor that of cadC in stem cells leads to the accumulation of harmful AP- and beta E-site intermediates.