7-(2-Deoxy-β-D-erythro-pentafuranosyl)-7H-imidazo[4,5-d][1,2,3]triazin-4-one | 56220-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 7-(2-Deoxy-β-D-erythro-pentafuranosyl)-7H-imidazo[4,5-d][1,2,3]triazin-4-one
• 英文别名: 9-(2-deoxy-β-D-ribofuranosyl)-2-azahypoxanthine；2-Aza-2'-deoxyinosine；7-(β-D-erythro-2-deoxy-pentofuranosyl)-3,7-dihydro-imidazo[4,5-d][1,2,3]triazin-4-one；7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-imidazo[4,5-d] [1,2,3]-triazin-4-one；2-Aza-2'-deoxyinosin；7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-imidazo[4,5-d]triazin-4-one
• CAS: 56220-50-9
• 化学式: C₉H₁₁N₅O₄
• 分子量: 253.217
• InChiKey: QFFLRMDXYQOYKO-KVQBGUIXSA-N

物化性质

• 密度：
  2.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2'-脱氧腺苷 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 NaOAc buffer 、 水 、 sodium acetate 、 溶剂黄146 、 sodium nitrite 、 calf intestine adenosine deaminase 作用下， 以 甘油 为溶剂， 反应 89.0h， 生成 7-(2-Deoxy-β-D-erythro-pentafuranosyl)-7H-imidazo[4,5-d][1,2,3]triazin-4-one
  参考文献：
  名称：

  2-氮杂-2'-脱氧腺苷：寡核苷酸的合成，碱基配对的选择性和堆积特性。

  摘要：

  2-Aza-2'-脱氧腺苷（2，z2Ad）是通过其1，N6-乙炔衍生物7合成的，并被酶法脱氨基形成2-aza-2'-脱氧肌苷（3）。化合物2被转化为亚磷酰胺结构单元10b。这用于固相寡核苷酸合成中。2-氮杂嘌呤碱基与鸟嘌呤形成强碱基对，而与腺嘌呤，胸腺嘧啶和胞嘧啶则弱得多。合成了在一个或两个末端带有悬空核苷酸残基的寡核苷酸双链体，例如2-aza-2'-脱氧腺苷和7-deaza-2'-脱氧腺苷（4，c7Ad），并且双链体的热稳定性为与悬挂的核苷酸残基的疏水性相关。

  DOI：

  10.1002/(sici)1521-3765(20000117)6:2<369::aid-chem369>3.0.co;2-2

文献信息

• Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells
  作者：Ivan Votruba、Antonín Holý、Hana Dvořáková、Jaroslav Günter、Dana Hocková、Hubert Hřebabecký、Tomas Cihlar、Milena Masojídková

  DOI：10.1135/cccc19942303

  日期：——

  Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs. All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N⁹-isomers in the purine and N¹-isomers in the pyrimidine series. Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety. The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N⁷-nitrogen atom. On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives. Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed. The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-dideoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-dideoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.

  藻酸盐凝胶包埋的辅助胸腺嘧啶依赖菌株大肠杆菌细胞催化2'-脱氧尿嘧啶的2-脱氧-D-核糖呋喃基团转移到嘌呤和嘧啶碱基以及它们的氮杂和去氮类似物。所有实验都不可避免地产生β-异构体；在大多数情况下，反应是区域特异性的，产生嘌呤中的N⁹-异构体和嘧啶系列中的N¹-异构体。此外，2,3-二脱氧核苷酸可以作为糖基团的供体。嘌呤碱基的受体活性仅在取代上有少许影响，唯一的条件是存在N⁷-氮原子。另一方面，在嘧啶系列中，活性仅限于大多数短链5-烷基和5-卤代尿嘧啶衍生物的狭窄选择。含氨基的杂环碱基会发生脱氨作用；可以通过将碱基转化为相应的N-二甲氨基甲烯基衍生物来避免这种情况，然后进行氨解作用。该方法通过分离腺嘌呤、鸟嘌呤、2-氯腺嘌呤、6-甲基嘌呤、8-氮杂腺嘌呤、8-氮杂鸟嘌呤、1-去氮腺嘌呤、3-去氮腺嘌呤的9-(2-脱氧-β-D-核糖呋喃基)衍生物，5-乙基尿嘧啶、5-氟尿嘧啶的1-(2-脱氧-β-D-核糖呋喃基)衍生物，以及9-(2,3-二脱氧-β-D-戊呋喃基)缺氧嘌呤、9-(2,3-二脱氧-β-D-戊呋喃基)-6-甲基嘌呤和其他核苷酸的验证。
• 2-azapurine compounds and their uses
  申请人：Seela Frank

  公开号：US20070015725A1

  公开（公告）日：2007-01-18

  Within oligonucleotides 2-azapurine and especially 2-azaadenine bases form specifically base pairs with guanine. This base pair is of analogous stability as an adenine-thymine but less stable than a guanine-cytosine base pair. Therefore, the incorporation of 2-azaadenine residues into oligonucleotides instead of cytosine leads specifically to hybridization complexes with nucleic acids with homogenous stability. This is useful for the adaptation of the stabilities of different oligonucleotide sequences in all kinds of hybridization techniques, for example in oligomer chip technology.

  在寡核苷酸内，2-氮杂嘌呤尤其是2-氮杂腺嘌呤碱基与鸟嘌呤形成特异性碱基对。这种碱基对的稳定性类似于腺嘌呤-胸腺嘧啶，但不如鸟嘌呤-胞嘧啶碱基对稳定。因此，将2-氮杂腺嘌呤残基纳入寡核苷酸中，而不是胞嘧啶，导致与同种稳定性的核酸形成特异性杂交复合物。这对于在各种杂交技术中适应不同寡核苷酸序列的稳定性非常有用，例如在寡聚物芯片技术中。
• Reagents, methods, and libraries for bead-based sequencing
  申请人：AB Advanced Genetic Analysis Corporation

  公开号：EP2003214A2

  公开（公告）日：2008-12-17

  The present invention provides methods for determining a nucleic acid sequence by performing successive cycles of duplex extension along a single stranded template. The cycles comprise steps of extension, ligation, and, preferably, cleavage. The invention provides methods of determining information about a sequence using at least two distinguishably labeled probe families.

  本发明提供了通过沿单链模板连续进行双链延伸循环来确定核酸序列的方法。这些循环包括延伸、连接和最好是裂解等步骤。本发明提供了使用至少两个可区分标记的探针系列确定序列信息的方法。
• Nucleic acid sequencing by performing successive cycles of duplex extension
  申请人：AB Advanced Genetic Analysis Corporation

  公开号：EP2233582A1

  公开（公告）日：2010-09-29

  The present invention provides methods for determining a nucleic acid sequence by performing successive cycles of duplex extension along a single stranded template. The cycles comprise steps of extension, ligation, and, preferably, cleavage. In certain embodiments the methods make use of extension probes containing phosphorothiolate linkages and employ agents appropriate to cleave such linkages. In certain embodiments the methods make use of extension probes containing an abasic residue or a damaged base and employ agents appropriate to cleave linkages between a nucleoside and an abasic residue and/or agents appropriate to remove a damaged base from a nucleic acid. The invention provides methods of determining information about a sequence using at least two distinguishably labeled probe families. In certain embodiments the methods acquire less than 2 bits of information from each of a plurality of nucleotides in the template in each cycle. In certain embodiments the sequencing reactions are performed on templates attached to beads, which are immobilized in or on a semi-solid support. The invention further provides sets of labeled extension probes containing phosphorothiolate linkages or trigger residues that are suitable for use in the method. In addition, the invention includes performing multiple sequencing reactions on a single template by removing initializing oligonucleotides and extended strands and performing subsequent reactions using different initializing oligonucleotides. The invention further provides efficient methods for preparing templates, particularly for performing sequencing multiple different templates in parallel. The invention also provides methods for performing ligation and cleavage. The invention also provides new libraries of nucleic acid fragments containing paired tags, and methods of preparing microparticles having multiple different templates (e.g., containing paired tags) attached thereto and of sequencing the templates individually. The invention also provides automated sequencing systems, flow cells, image processing methods, and computer-readable media that store computer-executable instructions (e.g., to perform the image-processing methods) and/or sequence information. In certain embodiments the sequence Information is stored in a database.

  本发明提供了通过沿单链模板连续进行双链延伸循环来确定核酸序列的方法。这些循环包括延伸、连接和最好是裂解等步骤。在某些实施方案中，该方法利用了含有硫代磷酸酯连接的延伸探针，并采用了适合裂解这种连接的制剂。在某些实施方案中，本发明的方法利用了含有缺失残基或受损碱基的延伸探针，并采用了适当的制剂来裂解核苷与缺失残基之间的连接和/或适当的制剂来去除核酸中的受损碱基。本发明提供了使用至少两个可区分标记的探针系列确定序列信息的方法。在某些实施方案中，这些方法在每个循环中从模板中的多个核苷酸中的每个核苷酸获取少于 2 比特的信息。在某些实施方案中，测序反应是在附着在珠子上的模板上进行的，珠子固定在半固体支持物中或半固体支持物上。本发明进一步提供了成套的标记延伸探针，这些探针含有适合在该方法中使用的硫代磷酸酯连接或触发残基。此外，本发明还包括通过移除初始化寡核苷酸和延伸链，并使用不同的初始化寡核苷酸进行后续反应，从而在单个模板上进行多个测序反应。本发明进一步提供了制备模板的高效方法，特别是并行执行多个不同模板测序的方法。本发明还提供了进行连接和裂解的方法。本发明还提供了含有成对标记的核酸片段的新文库，以及制备附有多个不同模板（如含有成对标记）的微颗粒并对模板进行单独测序的方法。本发明还提供了自动测序系统、流动池、图像处理方法以及存储计算机可执行指令（例如，执行图像处理方法）和/或序列信息的计算机可读介质。在某些实施例中，序列信息存储在数据库中。
• Reagents, methods and libraries for bead-based sequencing
  申请人：AB Advanced Genetic Analysis Corporation

  公开号：EP2236628A2

  公开（公告）日：2010-10-06

  The present invention provides methods for determining a nucleic acid sequence by performing successive cycles of duplex extension along a single stranded template. The cycles comprise steps of extension, ligation, and, preferably, cleavage. In certain embodiments the methods make use of extension probes containing phosphorothiolate linkages and employ agents appropriate to cleave such linkages. In certain embodiments the methods make use of extension probes containing an abasic residue or a damaged base and employ agents appropriate to cleave linkages between a nucleoside and an abasic residue and/or agents appropriate to remove a damaged base from a nucleic acid. The invention provides methods of determining information about a sequence using at least two distinguishably labeled probe families. In certain embodiments the methods acquire less than 2 bits of information from each of a plurality of nucleotides in the template in each cycle. In certain embodiments the sequencing reactions are performed on templates attached to beads, which are immobilized in or on a semi-solid support. The invention further provides sets of labeled extension probes containing phosphorothiolate linkages or trigger residues that are suitable for use in the method. In addition, the invention includes performing multiple sequencing reactions on a single template by removing initializing oligonucleotides and extended strands and performing subsequent reactions using different initializing oligonucleotides. The invention further provides efficient methods for preparing templates, particularly for performing sequencing multiple different templates in parallel. The invention also provides methods for performing ligation and cleavage. The invention also provides new libraries of nucleic acid fragments containing paired tags, and methods of preparing microparticles having multiple different templates (e.g., containing paired tags) attached thereto and of sequencing the templates individually. The invention also provides automated sequencing systems, flow cells, image processing methods, and computer-readable media that store computer-executable instructions (e.g., to perform the image-processing methods) and/or sequence information. In certain embodiments the sequence information is stored in a database.

  本发明提供了通过沿单链模板连续进行双链延伸循环来确定核酸序列的方法。这些循环包括延伸、连接和最好是裂解等步骤。在某些实施方案中，该方法利用了含有硫代磷酸酯连接的延伸探针，并采用了适合裂解这种连接的制剂。在某些实施方案中，本发明的方法利用了含有缺失残基或受损碱基的延伸探针，并采用了适当的制剂来裂解核苷与缺失残基之间的连接和/或适当的制剂来去除核酸中的受损碱基。本发明提供了使用至少两个可区分标记的探针系列确定序列信息的方法。在某些实施方案中，这些方法在每个循环中从模板中的多个核苷酸中的每个核苷酸获取少于 2 比特的信息。在某些实施方案中，测序反应是在附着在珠子上的模板上进行的，珠子固定在半固体支持物中或半固体支持物上。本发明进一步提供了成套的标记延伸探针，这些探针含有适合在该方法中使用的硫代磷酸酯连接或触发残基。此外，本发明还包括通过移除初始化寡核苷酸和延伸链，并使用不同的初始化寡核苷酸进行后续反应，从而在单个模板上进行多个测序反应。本发明进一步提供了制备模板的高效方法，特别是并行执行多个不同模板测序的方法。本发明还提供了进行连接和裂解的方法。本发明还提供了含有成对标记的核酸片段的新文库，以及制备附有多个不同模板（如含有成对标记）的微颗粒并对模板进行单独测序的方法。本发明还提供了自动测序系统、流动池、图像处理方法以及存储计算机可执行指令（例如，执行图像处理方法）和/或序列信息的计算机可读介质。在某些实施例中，序列信息存储在数据库中。