2-cyanoethyl N,N'-diisopropylphosphoramidochloridite | 151171-76-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-cyanoethyl N,N'-diisopropylphosphoramidochloridite
• 英文别名: 2-cyanoethyl N,N-diisopropylphosphonamidic chloride；3-[chloro-[di(propan-2-yl)amino]phosphoryl]propanenitrile
• CAS: 151171-76-5
• 化学式: C₉H₁₈ClN₂OP
• 分子量: 236.681
• InChiKey: JTMGWXAUNOAHCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl N,N'-diisopropylphosphoramidochloridite 、 1-[(2S,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-4-prop-2-enyloxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以77%的产率得到1-{3-C-allyl-3-O-[cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-erythro-pentofuranosyl}thymine
  参考文献：
  名称：

  Synthesis and hybridization properties of β- and α-oligodeoxynucleotides containing β- and α-1-(3-C-allyl-2-deoxy-D-erythro-pentofuranosyl)thymine and α-1-[3-C-(3-aminopropyl)-2-deoxy-D-erythro-pentofuranosyl]thymine

  摘要：

  本研究描述了δ-和δ-1-(3-C-烯丙基-2-脱氧-D-赤式戊呋喃糖基)胸腺嘧啶的聚合合成及其与δ-和δ-寡脱氧核苷酸（ODNs）的结合。对修饰的 ODN 与互补的单链 DNA 和 RNA 之间形成的双链体的热稳定性进行了评估。在所有情况下都能形成稳定的双链，但与相应的δ-ODN 参考双链相比，含有δ-3â²-C-烯丙基胸苷的δ-ODN 对 DNA 和 RNA 的热稳定性略有降低，而含有δ-3â²-C-烯丙基胸苷的δ-ODN 的热稳定性则显著提高。使用含有一个δ-1-[3-C-（3-氨基丙基）-2-脱氧-D-赤式戊呋喃糖基]胸腺嘧啶单体的δ-ODN，还能获得对 DNA 和 RNA 都更稳定的双链体。

  DOI：

  10.1039/a703173d

文献信息

• 5-Nitroindole oligonucleotides with alkynyl side chains: universal base pairing, triple bond hydration and properties of pyrene “click” adducts
  作者：Sachin A. Ingale、Peter Leonard、Haozhe Yang、Frank Seela

  DOI：10.1039/c4ob01478b

  日期：——

  with 3-ethynyl-5-nitroindole and 3-octadiynyl-5-nitroindole 2′-deoxyribonucleosides were prepared by solid-phase synthesis. To this end, nucleoside phosphoramidites with clickable side chains were synthesized. The 3-ethynylated 5-nitroindole nucleoside was hydrated during automatized DNA synthesis to 3-acetyl-5-nitroindole 2′-deoxyribonucleoside. Side product formation was circumvented by triisopropylsilyl

  通过固相合成制备具有3-乙炔基-5-硝基吲哚和3-辛二炔基-5-硝基吲哚2'-脱氧核糖核苷的寡核苷酸。为此，合成了具有可点击侧链的核苷亚磷酰胺。在自动DNA合成过程中，将3-乙炔基化的5-硝基吲哚核苷水合为3-乙酰基-5-硝基吲哚2'-脱氧核糖核苷。通过乙炔基侧链的三异丙基甲硅烷基保护来避免副产物的形成，并在寡核苷酸合成后用TBAF将其除去。具有可点击的5-硝基吲哚骨架的所有化合物均显示通用碱基配对，并且可以在DNA链的任何位置用几乎任何叠氮化物进行官能化。用1-叠氮基甲基py对侧链进行官能化得到点击加合物，其中荧光被5-硝基吲哚部分猝灭。然而，在双链体形成过程中，荧光略有恢复。具有pyr残基和长连接臂的寡核苷酸比具有未官能化侧链的寡核苷酸稳定。通过寡核苷酸中residue残基的紫外红移和建模研究，建立了长插入物加合物的pyr插层，与具有短侧链的那些相比，其显示出更高的双链稳定性。
• [EN] COMPOUNDS FOR THE SYNTHETIC INTRODUCTION OF N-ALKYL NUCLEOSIDES INTO DNA OLIGONUCLEOTIDES<br/>[FR] COMPOSÉS POUR L'INTRODUCTION SYNTHÉTIQUE DE N-ALKYLE NUCLÉOSIDES DANS DES OLIGONUCLÉOTIDES D'ADN
  申请人：BERRY & ASSOCIATES INC

  公开号：WO2012075005A1

  公开（公告）日：2012-06-07

  The present invention provides for compounds of Formula (I): wherein X-N and R1-R4 have any of the values disclosed in the specification. The compounds of Formula I are useful as reagents to introduce N-alkyl nucleosides into DNA oligonucleotides. The present invention also provides for methods of synthesizing the compounds of Formula (I).

  本发明提供了公式（I）的化合物：其中X-N和R1-R4具有规范中披露的任何值。公式I的化合物可用作试剂，将N-烷基核苷酸引入DNA寡核苷酸中。本发明还提供了合成公式（I）化合物的方法。
• 2′-Spiro ribo- and arabinonucleosides: synthesis, molecular modelling and incorporation into oligodeoxynucleotides
  作者：B. Ravindra Babu、Lise Keinicke、Michael Petersen、Claus Nielsen、Jesper Wengel

  DOI：10.1039/b306354b

  日期：——

  We have synthesized four conformationally restricted bicyclic 2'-spiro nucleosides via 2'-C-allyl nucleosides as key intermediates. The ribo-configured 2'-spironucleosides 9b and 14b were obtained by a convergent strategy starting from 2-ketofuranose 1 whereas the arabino-configured 2'-spironucleosides 21 and 27 were obtained by a linear strategy with a 2'-ketouridine derivative as starting material

  我们已经合成了通过2'-C-烯丙基核苷作为关键中间体的四个构象受限的双环2'-螺核苷。核糖构型的2'-螺旋核苷9b和14b是通过2-酮呋喃糖1的聚合策略获得的，而阿拉伯糖构型的2'-螺旋核苷21和27是通过以2'-酮尿苷衍生物为起始的线性策略获得的。材料。9b / 14b的呋喃糖环采用N-型构象，而21/27的呋喃糖环以N ＝ S平衡存在。这些化合物没有抗HIV-1活性或细胞毒性。使用亚磷酰胺方法在自动化DNA合成仪上将四个2'-螺核苷（作为单体X4和X5）掺入寡脱氧核苷酸中。不论单体结构如何，杂交研究表明，与相应的DNA：DNA和DNA：RNA双链体相比，这些2'-螺核苷酸单体（X4和X5）诱导的双链体热稳定性降低。分子建模表明，空间限制是修饰寡聚脱氧核苷酸对互补单链DNA和单链RNA互补物结合亲和力降低的可能原因。
• A Trisbenzimidazole Phosphoramidite Building Block Enables High-Yielding Syntheses of RNA-Cleaving Oligonucleotide Conjugates
  作者：Felix Zellmann、Michael W. Göbel

  DOI：10.3390/molecules25081842

  日期：——

  low yielding and not reliable. Here, a phosphoramidite building block is described that can be coupled to oligonucleotides by manual solid phase synthesis in total yields around 85%. Based on this chemistry, we have now studied the impact of LNA (locked nucleic acids) nucleotides on the rates and the site-specificities of RNA cleaving conjugates. The highest reaction rates and the most precise cuts

  当连接到寡核苷酸的 5' 末端时，RNA 切割催化剂三（2-氨基苯并咪唑）以高度位点特异性的方式切割互补的 RNA 链。先前通过使用催化剂的活性酯酰化氨基接头来实现缀合。然而，该程序产量低且不可靠。在这里，描述了一种亚磷酰胺结构单元，它可以通过手动固相合成与寡核苷酸偶联，总产率约为 85%。基于这种化学反应，我们现在研究了 LNA（锁核酸）核苷酸对 RNA 裂解偶联物的速率和位点特异性的影响。当催化剂连接到强大的 5' 闭合碱基对上并且寡核苷酸包含几个均匀分布在链中的 LNA 单元时，可以预期最高的反应速率和最精确的切割。然而，当放置在 5' 位置时，LNA 构建模块往往会降低 RNA 切割的特异性。
• METHOD FOR PREPARING DNA FRAGMENT HAVING STICKY END
  申请人：Komiyama Makoto

  公开号：US20110009607A1

  公开（公告）日：2011-01-13

  The present invention provides a method for preparing a DNA fragment, in which a desired double-stranded DNA fragment having a sticky end is directly and easily obtained from an amplification product (an amplified fragment) after PCR without a restriction enzyme digestion. The method for preparing a DNA fragment having a sticky end of the present invention comprises: (i) a step of performing a PCR reaction using a template DNA and specific primers to obtain an amplified DNA fragment; and (ii) a step of performing a prescribed treatment on the amplified DNA fragment to dissociate a protecting group from the fragment. Herein, the above-mentioned specific primers are composed of a complementary DNA portion consisting of a nucleotide sequence complementarily binding to an amplification target region in a template DNA and a non-complementary DNA portion consisting of a nucleotide sequence that links to the 5′ end of the complementary DNA portion but does not complementarily bind to the amplification target sequence, and at least a base corresponding to the 3′ end in the nucleotide sequence of the non-complementary DNA portion is modified with a protecting group capable of terminating the progression of DNA replication catalyzed by a DNA polymerase.

  本发明提供了一种制备DNA片段的方法，其中在PCR后，无需限制性内切酶消化，即可直接轻松地从扩增产物（扩增片段）中获得具有粘性末端的所需双链DNA片段。本发明的制备具有粘性末端的DNA片段的方法包括：（i）使用模板DNA和特异性引物进行PCR反应，以获得扩增的DNA片段；（ii）对扩增的DNA片段进行规定的处理，以使保护基从片段中解离。此处，上述特异性引物由互补DNA部分和非互补DNA部分组成。互补DNA部分包括与模板DNA中扩增目标区域互补配对的核苷酸序列，而非互补DNA部分包括连接到互补DNA部分5'端的核苷酸序列，但不与扩增目标序列互补配对，而且至少有一个与非互补DNA部分核苷酸序列中3'端相对应的碱基被保护基修饰，该保护基能够终止由DNA聚合酶催化的DNA复制的进展。