6-(triphenylmethylamino)hexanoic acid | 5612-13-5

• 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: 6-(triphenylmethylamino)hexanoic acid
• 英文别名: 6-triphenylmethylaminohexanoic acid；6-(tritylamino)caproic acid；6-(tritylamino)hexanoic acid
• CAS: 5612-13-5
• 化学式: C₂₅H₂₇NO₂
• 分子量: 373.495
• InChiKey: RIHLCYPQNGWANI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  6-(triphenylmethylamino)hexanoic acid 在 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 Ethyl 2-[[2-[6-(tritylamino)hexanoylamino]-1,3-thiazole-4-carbonyl]amino]-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  Ryabinin; Sinyakov, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 531 - 536

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氨基己酸 在 sodium hydroxide 、 氯化亚砜 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 6-(triphenylmethylamino)hexanoic acid
  参考文献：
  名称：

  Inhibition of HIV-1 integrase-catalysed reaction by new DNA minor groove ligands: the oligo-1,3-thiazolecarboxamide derivatives

  摘要：

  Human immunodeficiency virus type 1 (HIV-1) integrase (IN) is an essential enzyme in the life cycle of the retrovirus, responsible for catalysing the insertion of the viral genome into the host cell chromosome. For this reason it provides an attractive target for antiviral drug design. We synthesized a series of novel thiazole (Tz)-containing oligopeptides (TCOs; oligo-1,3-thiazolecarboxamides), specifically interacting within the minor groove of DNA. The oligocarboxamide derivatives contained 1-4 Tz rings and different N- and C-terminal groups. The effect of these oligocarboxamides on the HIV-1 IN-catalysed reaction was investigated. Some of the compounds were able to inhibit the reaction. The inhibitory effect of the TCOs increased with the number of Tz units. The structure of various additional positively and/or negatively charged groups attached to the N- and C-termini of TCOs had a pronounced effect on their interaction with the DNA substrate complexed to IN. Modified TCOs having a better affinity for this complex should provide a rationale for the design of drugs targeting the integration step. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01181-8

文献信息

• Selective binding complementary oligonucleotides
  申请人：Epoch Pharmaceuticals, Inc.

  公开号：US05912340A1

  公开（公告）日：1999-06-15

  In a matched pair of oligonucleotides (ODNS) each member of the pair is complementary or substantially complementary in the Watson Crick sense to a target sequence of duplex nucleic acid where the two strands of the target sequence are themselves complementary to one another. The ODNs include modified bases of such nature that the modified base forms a stable hydrogen bonded base pair with the natural partner base, but does not form a stable hydrogen bonded base pair with its modified partner. This is accomplished when in a hybridized structure the modified base is capable of forming two or more hydrogen bonds with its natural complementary base, but only one hydrogen bond with its modified partner. Due to the lack of stable hydrogen bonding with each other, the matched pair of oligonucleotides have a melting temperature under physiological or substantially physiological conditions of approximately 40.degree. C. or less. However each of the matched ODN pair of the invention forms a substantially stable hybrid with the target sequence in each strand of the duplex nucleic acid. The hybrids of target duplex nucleic acids formed with the ODN pairs of the invention are useful for gene mapping and in diagnostic and therapeutic applications.

  在一对配对的寡核苷酸（ODNS）中，每个成员的配对成员在沃森-克里克意义上与双链核酸的目标序列互补或基本互补，其中目标序列的两条链本身是互补的。ODNS包括具有这种性质的修饰碱基，即修饰碱基与天然配对碱基形成稳定的氢键配对，但与其修饰配对碱基不形成稳定的氢键配对。当在杂交结构中，修饰碱基能够与其天然互补碱基形成两个或更多氢键，但只能与其修饰配对碱基形成一个氢键时，就实现了这一点。由于彼此之间缺乏稳定的氢键结合，配对的寡核苷酸在生理条件或基本生理条件下的熔化温度约为40摄氏度或更低。然而，本发明的每一对匹配的ODN对都与双链核酸的每条链中的目标序列形成基本稳定的杂交。使用本发明的ODN对形成的目标双链核酸的杂交对于基因定位以及诊断和治疗应用是有用的。
• Cross-linking oligonucleotides
  申请人：EPOCH Pharmaceuticals, Inc.

  公开号：US05824796A1

  公开（公告）日：1998-10-20

  This invention is directed to novel substituted nucleotide bases with a crosslinking arm which accomplish crosslinking between specific sites on adjoining strands of oligonucleotides or oligodeoxynucleotides. The invention is also directed to oligonucleotides comprising at least one of these crosslinking agents and to the use of the resulting novel oligonucleotides for diagnostic and therapeutic purposes. The crosslinking agents of the invention are of the following formula (I'): R.sub.1 --B--(CH.sub.2).sub.q --(Y).sub.r --(CH.sub.2).sub.m --A'(I') wherein, R.sub.1 is hydrogen, or a sugar moiety or analog thereof optionally substituted at its 3' or its 5' position with a phosphorus derivative attached to the sugar moiety by an oxygen and including groups Q.sub.1 Q.sub.2 and Q.sub.3 or with a reactive precursor thereof suitable for nucleotide bond formation; Q.sub.1 is hydroxy, phosphate or diphosphate; Q.sub.2 is .dbd.O or .dbd.S; Q.sub.3 is CH.sub.2 --R', S--R', O--R', or N--R'R"; each of R' and R" is independently hydrogen or C.sub.1-6 alkyl; B is a nucleic acid base or analog thereof that is a component of an oligonucleotide; Y is a functional linking group; each of m and q is independently 0 to 8, inclusive; r is 0 or 1; and A' is a leaving group. This invention is also directed to novel 3,4-disubstituted and 3,4,-trisubstituted pyrazolo\x9b3,4-d!-pyrimidines and to the use of these nucleic acid bases in the preparation of oligonucleotides. The invention includes nucleosides and mono- and oligonucleotides comprising at least one of these pyrazolopyrimidines, and to the use of the resulting novel oligonucleotides for diagnostic purposes.

  这项发明涉及一种新型的取代核苷酸碱基，具有交联臂，能够在寡核苷酸或寡脱氧核苷酸的相邻链上的特定位点之间实现交联。该发明还涉及包含至少一种这些交联剂的寡核苷酸，以及利用由此产生的新型寡核苷酸进行诊断和治疗的用途。该发明的交联剂具有以下式(I')：R₁--B--(CH₂)q--(Y)r--(CH₂)m--A'（I'），其中，R₁是氢，或者是糖基或其类似物，在其3'或5'位置可选择性地取代为通过氧原子连接到糖基的磷衍生物，包括基团Q₁、Q₂和Q₃，或者其适用于核苷酸键形成的反应前体；Q₁是羟基、磷酸酯或二磷酸酯；Q₂是.dbd.O或.dbd.S；Q₃是CH₂--R'、S--R'、O--R'或N--R'R"，其中R'和R"各自独立地是氢或C₁-₆烷基；B是核酸碱基或其类似物，是寡核苷酸的组成部分；Y是功能性连接基团；m和q各自独立地为0至8（包括8）；r为0或1；A'是一个脱离基团。该发明还涉及新型的3,4-二取代和3,4-三取代吡唑嘧啶，以及在制备寡核苷酸中使用这些核酸碱基。该发明包括含有至少一种这些吡唑嘧啶的核苷和单核苷酸、寡核苷酸，以及利用由此产生的新型寡核苷酸进行诊断的用途。
• Crosslinking oligonucleotides
  申请人：Epoch Pharmaceuticals, Inc.

  公开号：US05849482A1

  公开（公告）日：1998-12-15

  Oligonucleotides (ODNs) include a sequence that is complementary to a target sequence in single stranded RNA, or single or double stranded DNA, and an alkylating function which after hybridization alkylates the target sequence. ODNs adapted for alkylating single stranded RNA, such as messenger RNA, are complementary to the target sequence in the Watson Crick sense. ODNs adapted for alkylating double stranded DNA have at least two alkylating functions and are complementary to the target sequence in the Hoogsteen or reverse Hoogsteen sense. With these ODNs both strands of the target sequence are alkylated. A third class of ODNs have at least approximately 26 nucleotide units in a continous sequence which are complementary to the target sequence of double stranded DNA, and the alkylating function is covalently attached to a nucleotide unit in the continuous sequence. Alkylation or cross-linking with this class of ODNs occurs in the presence of a recombinase enzyme.

  寡核苷酸（ODNs）包括一个与单链RNA、单链或双链DNA中的目标序列互补的序列，以及一个烷基化功能，在杂交后烷基化目标序列。适用于烷基化单链RNA（如信使RNA）的ODNs在沃森-克里克意义上与目标序列互补。适用于烷基化双链DNA的ODNs至少具有两个烷基化功能，并且在胡格斯汀或反向胡格斯汀意义上与目标序列互补。使用这些ODNs，目标序列的两条链都会被烷基化。第三类ODNs具有至少大约26个核苷酸单元的连续序列，与双链DNA的目标序列互补，且烷基化功能共价连接到连续序列中的一个核苷酸单元上。在存在重组酶的情况下，使用这类ODNs进行烷基化或交联。
• Libraries of oligomers labelled with different tags
  申请人：OXFORD GENE TECHNOLOGY IP LIMITED

  公开号：EP1428810A2

  公开（公告）日：2004-06-16

  A method of making a set of labelled compounds by the use of a preferably particulate support, comprises dividing the support into lots, performing a different chemical reaction on each lot of the support, e.g. to couple a chemical moiety to that lot of the support, tagging a fraction of each lot of the support with a different label, and combining the said lots of the support. The steps are repeated several times, preferably to build up oligomer molecules carrying labels which identify the nature and position of a monomer unit of the oligomer, and which are releasable from the support. Preferred labels, which are releasable from the compounds by cleavage to provide charged groups for analysis by mass spectrometry, are groups of the trityl (trimethylphenyl) family. Also claimed are libraries of these labels and their use in assays and nucleic acid analysis methods.

  使用一种最好是颗粒状的载体来制造一组标记化合物的方法，包括将载体分成若干批次，在每批载体上进行不同的化学反应，例如将化学分子与该批载体耦合，用不同的标签标记每批载体的一部分，然后将所述批次的载体合并。这些步骤重复多次，最好能形成带有标签的低聚物分子，这些标签可识别低聚物单体单元的性质和位置，并可从支撑物上释放。首选的标签是三甲基苯基基团，这些标签可通过裂解从化合物中释放出来，从而提供带电基团用于质谱分析。本发明还涉及这些标签的文库及其在检测和核酸分析方法中的应用。
• Libraries of oligomers labeled with different tags
  申请人：Southern Mellor Edwin

  公开号：US20050003408A1

  公开（公告）日：2005-01-06

  A method of making a set of labelled compounds by the use of a preferably particulate support, comprises dividing the support into lots, performing a different chemical reaction on each lot of the support, e.g. to couple a chemical moiety to that lot of the support, tagging a fraction of each lot of the support with a different label, and combining the said lots of the support. The steps are repeated several times, preferably to build up oligomer molecules carrying labels which identify the nature and position of a monomer unit of the oligomer, and which are releasable from the support. Preferred labels, which are releasable from the compounds by cleavage to provide charged groups for analysis by mass spectrometry, are groups of the trityl (trimethylphenyl) family. Also claimed are libraries of these labels is and their use in assays and nucleic acid analysis methods.

  使用一种最好是颗粒状的载体来制造一组标记化合物的方法，包括将载体分成若干批次，在每批载体上进行不同的化学反应，例如将化学分子与该批载体耦合，用不同的标签标记每批载体的一部分，然后将所述批次的载体合并。这些步骤重复多次，最好能形成带有标签的低聚物分子，这些标签可识别低聚物单体单元的性质和位置，并可从支撑物上释放。可通过裂解从化合物中释放出来，从而提供带电基团用于质谱分析的首选标签是三甲基苯基（trimethylphenyl）基团。本发明还涉及这些标签的文库及其在检测和核酸分析方法中的应用。