2',3'-二脱氧腺苷5'-三磷酸酯 | 24027-80-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 中文名称: 2',3'-二脱氧腺苷5'-三磷酸酯
• 英文名称: 2',3'-dideoxyadenosine 5'-triphosphate
• 英文别名: ddATP；2',3'-Dideoxy-ATP；[[[(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-oxidophosphoryl]oxy-oxoniophosphoryl]oxy-oxoniophosphinate
• CAS: 24027-80-3
• 化学式: C₁₀H₁₆N₅O₁₁P₃
• 分子量: 475.185
• InChiKey: OAKPWEUQDVLTCN-NKWVEPMBSA-N

物化性质

• 沸点：
  843.5±75.0 °C(Predicted)
• 密度：
  2.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  239
• 氢给体数：
  5
• 氢受体数：
  15

制备方法与用途

生物活性方面，ddATP 是一种双脱氧核苷酸，能够作为 DNA 聚合酶（DNA聚合酶）的链延伸抑制剂。它常用于 Sanger 方法进行 DNA测序。

反应信息

• 作为反应物：
  描述：

  2',3'-二脱氧腺苷5'-三磷酸酯 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Terminal Phosphate-Labeled Nucleotides with Improved Substrate Properties for Homogeneous Nucleic Acid Assays

  摘要：

  Nucleotides with a dye attached to the terminal phosphate with four or more phosphates (tetra- or pentaphosphates) are superior substrates than the corresponding triphosphates for DNA and RNA polymerases. When fluorogenic dyes are directly attached to the terminal phosphate, they can be released by the action of polymerase and alkaline phosphatase. The released dye changes color and fluorescence properties. The fluorescent signal can also be amplified by using multiple labeled nucleotides to detect small amounts of template. We have explored the utility of these nucleotides in a variety of applications including homogeneous SNP detection methods, DNA sequencing, and quantitation of PCR and RCA.

  DOI：

  10.1021/ja043595x

文献信息

• MASSIVE PARALLEL METHOD FOR DECODING DNA AND RNA
  申请人：The Trustees of Columbia University in the City of New York

  公开号：US20160264612A1

  公开（公告）日：2016-09-15

  This invention provides methods for attaching a nucleic acid to a solid surface and for sequencing nucleic acid by detecting the identity of each nucleotide analogue after the nucleotide analogue is incorporated into a growing strand of DNA in a polymerase reaction. The invention also provides nucleotide analogues which comprise unique labels attached to the nucleotide analogue through a cleavable linker, and a cleavable chemical group to cap the —OH group at the 3′-position of the deoxyribose.

  这项发明提供了一种将核酸连接到固体表面的方法，以及通过在聚合酶反应中将核苷酸类似物并入到DNA增长链中后检测每个核苷酸类似物的身份来测序核酸的方法。该发明还提供了包含独特标签的核苷酸类似物，通过可切割的连接剂连接到核苷酸类似物上，并且包含用于封闭去氧核糖的3′-位置上的—OH基团的可切割化学基团。
• Fluorescent nucleobase conjugates having anionic linkers
  申请人：PE Corporation (NY)

  公开号：US20020102590A1

  公开（公告）日：2002-08-01

  Provided are nucleotide-dye conjugates and related compounds in which a dye is linked to a nucleobase directly or indirectly by an anionic linker. The anionic character of the linker is provided by one or more anionic moieties which are present in the linker, such as phosphate, phosphonate, sulfonate, and carboxylate groups. When the dye is a provided as a donor/acceptor dye pair, the anionic linker can be located between the donor and the acceptor, or between the nucleobase and either the donor or acceptor, or both. In one embodiment, conjugates of the invention provide enhanced electrophoretic mobility characteristics to sequencing fragments, e.g., for dideoxy sequencing using labeled terminators.

  提供了核苷酸染料共轭物和相关化合物，其中染料通过阴离子连接物直接或间接地与核碱基相连。连接物的阴离子性质由连接物中存在的一个或多个阴离子基团提供，例如磷酸酯基、膦酸酯基、磺酸基和羧酸基。当染料作为给体/受体染料对提供时，阴离子连接物可以位于给体和受体之间，或者位于核碱基和给体或受体之间，或两者之间。在一种实施方案中，本发明的共轭物提供了增强的电泳迁移特性，例如，用标记终止子进行二氧基测序的测序片段。
• Broad specificity of human phosphoglycerate kinase for antiviral nucleoside analogs
  作者：Sarah Gallois-Montbrun、Abdesslem Faraj、Edward Seclaman、Jean-Pierre Sommadossi、Dominique Deville-Bonne、Michel Véron

  DOI：10.1016/j.bcp.2004.06.012

  日期：2004.11

  the activation of L-nucleoside analogs, a new class of anticancer and antiviral agents. J Biol Chem 2003;278:36726-32]. In the present work, we extended the enzymatic study of human PGK specificity to purine and pyrimidine nucleotide derivatives in both D- and L-configuration. Human PGK demonstrated catalytic efficiencies in the 10(4)-10(5)M(-1)s(-1) range for purine ribo-, deoxyribo- and dideoxyribonucleotide

  抗病毒治疗中使用的核苷类似物需要磷酸化为三磷酸对应物，才能在其细胞靶标上具有活性。最近报道了人磷酸甘油酸激酶（hPGK）参与胞苷L-核苷酸衍生物的磷酸化的最后步骤[Krishnan PGE，Lam W，Dutschman GE，Grill SP，Cheng YC。3-磷酸​​甘油酸激酶（一种糖酵解酶）在新型抗癌和抗病毒药物L-核苷类似物的激活中具有新作用。生物化学杂志2003； 278：36726-32]。在目前的工作中，我们将人PGK特异性的酶学研究扩展到了D-和L-构型的嘌呤和嘧啶核苷酸衍生物。人类PGK对嘌呤核糖，脱氧核糖和双脱氧核糖核苷酸衍生物的催化效率在10（4）-10（5）M（-1）s（-1）范围内，在D或L配置中。相反，它与天然嘧啶D-核苷酸（少于10（3）M（-1）s（-1））的活性差。嘧啶L对映体是有希望的针对B型肝炎的治疗类似物，其底物是其D对映体的2-25倍。人类PG
• 4,7-dichlororhodamine dyes labeled polynucleotides
  申请人：Lee G. Linda

  公开号：US20050112781A1

  公开（公告）日：2005-05-26

  A set of 4,7-dichlororhodamine compounds useful as fluorescent dyes are disclosed having the structures wherein R 1 -R 6 are hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, linking group, or, when taken together, R 1 and R 6 is benzo, or, when taken together, R 4 and R 5 is benzo; R 7 -R 10 , R 12 -R 16 and R 18 may be hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, amido, nitrile, lower alkoxy, linking group; R 11 and R 17 may be hydrogen, lower alkyl, lower alkene, lower alkyne, phenyl, aryl, linking group; Y 1 -Y 4 are hydrogen, lower alkyl, or cycloalkyl, or, when taken together, Y 1 and R 2 , Y 2 and R 1 Y 3 and R 3 , and/or Y 4 and R 4 is propano, ethano, or substituted forms thereof, and X 1 -X 3 taken separately are hydrogen, chlorine, fluorine, lower alkyl, carboxylate, sulfonate, hydroxymethyl, and linking group, or any combinations thereof. In another aspect, the invention includes reagents labeled with the 4,7-dichlororhodamine dye compounds, including deoxynucleotides, dideoxynucleotides, and polynucleotides. In an additional aspect, the invention includes methods utilizing such dye compounds and reagents including dideoxy polynucleotide sequencing and fragment analysis methods.

  本文披露了一组4,7-二氯罗丹明化合物的结构，可用作荧光染料，其中R1-R6为氢、氟、氯、较低烷基、较低烯烃、较低炔烃、磺酸酯、砜、氨基、酰胺、腈、较低烷氧基、连接基或在一起时，R1和R6为苯并或在一起时，R4和R5为苯并；R7-R10、R12-R16和R18可以是氢、氟、氯、较低烷基、较低烯烃、较低炔烃、磺酸酯、砜、氨基、酰胺、腈、较低烷氧基、连接基；R11和R17可以是氢、较低烷基、较低烯烃、较低炔烃、苯基、芳基、连接基；Y1-Y4可以是氢、较低烷基或环烷基，或在一起时，Y1和R2、Y2和R1、Y3和R3和/或Y4和R4为丙烷、乙烷或其取代形式，而X1-X3单独取为氢、氯、氟、较低烷基、羧酸盐、磺酸盐、羟甲基和连接基，或任何组合。在另一个方面，本发明还包括用4,7-二氯罗丹明染料化合物标记的试剂，包括脱氧核苷酸、二脱氧核苷酸和多核苷酸。在另一个方面，本发明还包括利用这种染料化合物和试剂的方法，包括二脱氧多核苷酸测序和片段分析方法。
• Propargylethoxyamino nucleotide primer extensions
  申请人：The Perkin-Elmer Corporation

  公开号：US20020045180A1

  公开（公告）日：2002-04-18

  Propargylethoxyamino nucleosides are disclosed having the structure 1 wherein R 1 and R 2 are —H, lower alkyl, or label; B is a 7-deazapurine, purine, or pyrimidine nucleoside base; W 1 is —H or —OH; W 2 is —OH or a moiety which renders the nucleoside incapable of forming a phosphodiester bond at the 3′-position; and W 3 is —PO 4 , —P 2 O 7 , —P 3 O 10 , phosphate analog, or —OH. Additionally, a primer extension method is provided employing the above propargylethoxyamino nucleosides.

  本文披露了具有以下结构的丙炔乙氧氨基核苷：其中R1和R2为—H、低碳基或标记；B为7-脱氮嘌呤、嘌呤或嘧啶核苷碱基；W1为—H或—OH；W2为—OH或一种使核苷酸无法在3'-位点形成磷酸二酯键的基团；W3为—PO4、—P2O7、—P3O10、磷酸盐类似物或—OH。此外，还提供了一种使用上述丙炔乙氧氨基核苷的引物延伸方法。