DMT-Serinol(H)-(OH) | 213550-25-5

• 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: DMT-Serinol(H)-(OH)
• 英文别名: (2R)-2-Amino-3-[bis(4-methoxyphenyl)phenylmethoxy]-1-propanol；(2R)-2-amino-3-[bis(4-methoxyphenyl)-phenylmethoxy]propan-1-ol
• CAS: 213550-25-5
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: NSESDOQTZQNHLZ-OAQYLSRUSA-N

物化性质

• 沸点：
  592.6±50.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  DMT-Serinol(H)-(OH) 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Diisopropyl-phosphoramidous acid (S)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetylamino]-propyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  丝氨酸醇衍生的无环核苷类似物掺入寡核苷酸：对双链体和三链体形成的影响

  摘要：

  亚磷酰胺6a-c易于通过原始方法制备，并用于将丝氨酸衍生的单元I-III掺入寡核苷酸中，与其天然类似物相比，它们在双链和三链体形成中的htbridization能力降低。

  DOI：

  10.1016/s0040-4039(98)01268-4
• 作为产物：
  描述：

  (S)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-(2,2,2-trifluoro-acetylamino)-propionic acid ethyl ester 在 sodium tetrahydroborate 、 lithium chloride 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 DMT-Serinol(H)-(OH)
  参考文献：
  名称：

  Synthesis and Evaluation of RNA Transesterification Efficiency Using Stereospecific Serinol-Terpyridine Conjugates

  摘要：

  Six novel artificial ribonucleases were synthesized employing a stereochemically pure abasic serinol backbone residue for attachment of the RNA transesterification agent copper(II) terpyridine. These stereochemically pure abasic residues were synthesized as phosphoramidite building blocks from the parent L-serine and D-serine starting building blocks and incorporated into oligonucleotides via solid-phase DNA synthesis. These artificial ribonucleases were constructed to determine if the stereochemistry of the alpha carbon of an abasic serinol residue has influence over RNA transesterification through selective placement of a pendant transesterification agent in either the major or minor groove. The novel artificial ribonucleases and previously synthesized artificial ribonucleases were challenged with a 28-mer and 159-mer RNA substrate. It was determined that the stereochemistry of the carbon atom derived from the a-carbon of serine did not influence the extent of cleavage in these studies using copper(II) terpyridine conjugated artificial ribonucleases.

  DOI：

  10.1080/15257770500230426

文献信息

• [EN] siRNAs WITH AT LEAST TWO LIGANDS AT DIFFERENT ENDS<br/>[FR] ARNSI POSSÉDANT AU MOINS DEUX LIGANDS À DEUX EXTRÉMITÉS DISTINCTES
  申请人：SILENCE THERAPEUTICS GMBH

  公开号：WO2019193189A1

  公开（公告）日：2019-10-10

  There is provided inter alia a conjugate for inhibiting expression of a target gene in a cell, said conjugate comprising a nucleic acid portion and ligand portions, said nucleic acid portion comprising at least one duplex region that comprises at least a portion of a first RNA strand and at least a portion of a second RNA strand that is at least partially complementary to the first strand, wherein said first strand is at least partially complementary to at least a portion of RNA transcribed from said target gene, said ligand portions comprising a linker moiety and a targeting ligand for in vivo targeting of cells and being conjugated exclusively to the 3' and/or 5' ends of one or both RNA strands, wherein the 5' end of the first RNA strand is not conjugated, wherein: (i) the second RNA strand is conjugated at the 5' end to the targeting ligand, and wherein (a) the second RNA strand is also conjugated at the 3' end to the targeting ligand and the 3' end of the first RNA strand is not conjugated; or (b) the first RNA strand is conjugated at the 3' end to the targeting ligand and the 3' end of the second RNA strand is not conjugated; or (c) both the second RNA strand and the first RNA strand are also conjugated at the 3' ends to the targeting ligand; or (ii) both the second RNA strand and the first RNA strand are conjugated at the 3' ends to the targeting ligand and the 5' end of the second RNA strand is not conjugated.

  提供了一种用于抑制细胞中靶基因表达的共轭物，该共轭物包括核酸部分和配体部分，所述核酸部分包括至少一个双链区域，该区域包括至少部分第一RNA链和至少部分第二RNA链，该第二RNA链至少部分与第一链互补，其中所述第一链至少部分与从所述靶基因转录的RNA的至少部分互补，所述配体部分包括连接子基团和用于体内细胞靶向的靶向配体，并且仅连接到一个或两个RNA链的3'和/或5'末端，其中第一RNA链的5'末端未连接，其中：(i) 第二RNA链在5'末端连接到靶向配体，其中(a) 第二RNA链还在3'末端连接到靶向配体，且第一RNA链的3'末端未连接；或(b) 第一RNA链在3'末端连接到靶向配体，且第二RNA链的3'末端未连接；或(c) 第二RNA链和第一RNA链的3'末端均连接到靶向配体；或(ii) 第二RNA链和第一RNA链的3'末端均连接到靶向配体，且第二RNA链的5'末端未连接。
• Probes comprising fluorescent artificial nucleobases and use thereof for detection of single base alteration
  申请人：Seitz Oliver

  公开号：US09206218B2

  公开（公告）日：2015-12-08

  The present invention relates to forced intercalation probes (FIT-probes) comprising at least one nucleoside analog which comprises at least a fluorescent artificial nucleobase directly bound to a carbon of a modified sugar moiety wherein said modified sugar moiety is a carba-sugar or an amino acid nucleic acid (AANA). Thereby the nucleoside analog is incorporated into DNA or RNA in the place of a single native base.

  本发明涉及强制插入探针(FIT-探针)，包括至少一个核苷类似物，该核苷类似物包括至少一个荧光人工碱基，直接结合到一个修饰糖基的碳上，所述修饰糖基是一个碳酸糖或一种氨基酸核酸(AANA)。因此，该核苷类似物被插入到DNA或RNA中，代替一个单个的天然碱基。
• Control of the Chirality and Helicity of Oligomers of Serinol Nucleic Acid (SNA) by Sequence Design
  作者：Hiromu Kashida、Keiji Murayama、Takasuke Toda、Hiroyuki Asanuma

  DOI：10.1002/anie.201006498

  日期：2011.2.7

  Mimicking the masters: An artificial nucleic acid, serinol nucleic acid (SNA), formed oligomers in which natural nucleobases were tethered through its 2‐amino‐1,3‐propanediol (serinol) scaffold. These SNA oligomers have two unique properties: their chirality is controllable by sequence design and can be inverted by reversing the sequence (see picture), and they can cross‐hybridize with DNA and RNA

  模仿大师：人工核酸丝氨醇核酸（SNA）形成了寡聚体，其中天然核碱基通过其2-氨基-1,3-丙二醇（serinol）支架被束缚。这些SNA低聚物具有两个独特的特性：它们的手性可通过序列设计控制，并且可以通过反转序列来反转（参见图片），并且它们可以与DNA和RNA杂交并具有足够的热稳定性。
• Designed thiazole orange nucleotides for the synthesis of single labelled oligonucleotides that fluoresce upon matched hybridization
  作者：Lucas Bethge、Ishwar Singh、Oliver Seitz

  DOI：10.1039/c000697a

  日期：——

  However, most previously reported dye–DNA conjugates showed only little if any difference between the fluorescence of the single and the double stranded state. Here, we introduce a TO-containing acyclic nucleotide, which is coupled during automated oligonucleotide synthesis and provides for the desired fluorescence-up properties. The study reveals the conjugation mode as the most important issue. We show

  诊断和基础研究中使用能够检测特定DNA序列的探针分子。大多数方法依赖于杂交反应的特异性，这使低温下单碱基突变的检测复杂化。在寡核苷酸的开发方面已经做出了巨大的努力，该寡核苷酸可以在匹配和错配探针-靶标复合物共存的温度下区分单碱基突变。包含对环境敏感的荧光染料（例如噻唑橙（TO））的寡核苷酸可提供单核苷酸特异性荧光。但是，大多数以前报道的染料-DNA偶联物在单链和双链状态的荧光之间仅显示出很小的差异。在这里，我们介绍一个包含TO的无环核苷酸，在自动化寡核苷酸合成过程中偶联，并提供所需的荧光增强特性。研究揭示了共轭模式是最重要的问题。我们展示了一种设计，该设计导致未结合的探针（背景）的荧光较低，但允许TO在探针-靶标复合物形成后采用荧光结合模式。在这些探针中，到取代规范的核碱基。请注意，“到当基本不匹配的位置紧邻时，“ – base”保持较低。
• [EN] NUCLEIC ACIDS FOR INHIBITING EXPRESSION OF PROS1 IN A CELL<br/>[FR] ACIDES NUCLÉIQUES POUR INHIBER L'EXPRESSION DE PROS1 DANS UNE CELLULE
  申请人：UNIV BERN

  公开号：WO2020225301A1

  公开（公告）日：2020-11-12

  The invention relates to nucleic acid products that interfere with PROS1 gene expression or inhibit its expression. The nucleic acids are particularly for use in the treatment, prevention or reduction of risk of suffering from a bleeding disorder.

  该发明涉及干扰PROS1基因表达或抑制其表达的核酸产品。这些核酸特别用于治疗、预防或减少患出血障碍的风险。