2-cyanoethyl pent-4-yn-1-yl diisopropylphosphaoramidite | 956093-25-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyanoethyl pent-4-yn-1-yl diisopropylphosphaoramidite
• 英文别名: O-4-pentynyl-O0-(2-cyanoethyl)-N,N-diisopropylphosphoramidite；O-[(2-cyanoethyl)-N,N-diisopropyl-phosphoramidite]-4-pentyn-1-ol；3-[[Di(propan-2-yl)amino]-pent-4-ynoxyphosphanyl]oxypropanenitrile；3-[[di(propan-2-yl)amino]-pent-4-ynoxyphosphanyl]oxypropanenitrile
• CAS: 956093-25-7
• 化学式: C₁₄H₂₅N₂O₂P
• 分子量: 284.338
• InChiKey: UZWDBMSZJCSVAI-UHFFFAOYSA-N

物化性质

• 沸点：
  321.7±27.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl pent-4-yn-1-yl diisopropylphosphaoramidite 在 氨 、 水 作用下， 反应 1.5h， 生成
  参考文献：
  名称：

  Azide Solid Support for 3′-Conjugation of Oligonucleotides and Their Circularization by Click Chemistry

  摘要：

  A solid support bearing an azido linker was used to synthesize a 3'-azido-alkyl-oligonucleotide by phosphoramidite chemistry. The resulting oligonucleotide was either conjugated by 1,3-dipolar cycloaddition on solid support or in solution with mannose-propargyl derivative and in solution with dansyl propargyl. Besides, after introduction of an alkyne function at the 5'-end, the resulting oligonucleotide hearing both 3'-azide and 5'-alkyne functions was circularized.

  DOI：

  10.1021/jo9014563
• 作为产物：
  描述：

  4-戊炔-1-醇 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以60 %的产率得到2-cyanoethyl pent-4-yn-1-yl diisopropylphosphaoramidite
  参考文献：
  名称：

  用于 GPI 生物学研究的双功能化糖基磷脂酰肌醇 (GPI) 锚的合成

  摘要：

  通过收敛策略合成了含有光敏基团和可点击基团的双功能糖基磷脂酰肌醇衍生物。

  DOI：

  10.1002/chem.202203457

文献信息

• [EN] GLYCOCLUSTERS AND THEIR PHARMACEUTICAL USE AS ANTIBACTERIALS<br/>[FR] GLYCOCLUSTERS ET LEUR UTILISATION PHARMACEUTIQUE COMME ANTIBACTÉRIENS
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2015040209A1

  公开（公告）日：2015-03-26

  A molecule responding to formula (I)of the glycocluster type with galactose residues at their extremities. Simple and efficient methods for the preparation of these compounds. Medical use of compounds (I) as inhibitors of infections by Pseudomonas aeruginosa, more specifically as inhibitors of Pseudomonas aeruginosa's virulence.

  一种分子对具有半乳糖残基的糖团型式（I）做出响应。这些化合物的制备有简单高效的方法。将化合物（I）用作铜绿假单胞菌感染的抑制剂，更具体地说是铜绿假单胞菌毒力的抑制剂。
• METHOD FOR THE SYNTHESIS OF OLIGONUCLEOTIDE DERIVATIVES
  申请人：Morvan Francois

  公开号：US20090124571A1

  公开（公告）日：2009-05-14

  Method for the synthesis of nucleotide derivatives wherein molecules of interest are grafted on the oligonucleotide with the help of a “click chemistry” reaction between an azide function on the molecule of interest and an alkyne function on the oligonucleotide, or between an alkyne function on the molecule of interest and an azide function on the oligonucleotide. Intermediate molecules, notably alkyne functionalized oligonucleotides, grafted oligonucleotides, azide functionalized oligonucleotides, oligonucleotide micro arrays containing them and the use of those grafted oligonucleotides for biological investigation and for cell targeting.

  核苷酸衍生物合成方法，其中感兴趣的分子通过“点击化学”反应被嫁接到寡核苷酸上，该反应在感兴趣分子上的偶氮功能与寡核苷酸上的炔基功能之间，或者在感兴趣分子上的炔基功能与寡核苷酸上的偶氮功能之间进行。中间分子，特别是炔基功能化的寡核苷酸，嫁接的寡核苷酸，偶氮功能化的寡核苷酸，包含它们的寡核苷酸微阵列以及利用这些嫁接的寡核苷酸进行生物研究和细胞靶向的用途。
• Glycoclusters and their pharmaceutical use as antibacterials
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2851371A1

  公开（公告）日：2015-03-25

  A molecule responding to formula (I) of the glycocluster type with galactose residues at their extremities. Simple and efficient methods for the preparation of these compounds. Medical use of compounds (I) as inhibitors of infections by Pseudomonas aeruginosa, more specifically as inhibitors of Pseudomonas aeruginosa's virulence.

  一种分子对糖团类型的公式（I）作出反应，其末端带有半乳糖残基。制备这些化合物的简单高效方法。化合物（I）作为铜绿假单胞菌感染的抑制剂的医药用途，更具体地作为铜绿假单胞菌毒力的抑制剂。
• Mannose-centered aromatic galactoclusters inhibit the biofilm formation of Pseudomonas aeruginosa
  作者：Caroline Ligeour、Olivier Vidal、Lucie Dupin、Francesca Casoni、Emilie Gillon、Albert Meyer、Sébastien Vidal、Gérard Vergoten、Jean-Marie Lacroix、Eliane Souteyrand、Anne Imberty、Jean-Jacques Vasseur、Yann Chevolot、François Morvan

  DOI：10.1039/c5ob00948k

  日期：——

  Two galactosylated glycoclusters show high affinity for LecA fromPseudomonas aeruginosaand anti-biofilm activity.

  两个半乳糖基糖团对来自铜绿假单胞菌的LecA具有很高的亲和力，并具有抗生物膜活性。
• Synthesis of branched-phosphodiester and mannose-centered fucosylated glycoclusters and their binding studies with Burkholderia ambifaria lectin (BambL)
  作者：Caroline Ligeour、Aymeric Audfray、Emilie Gillon、Albert Meyer、Nicolas Galanos、Sébastien Vidal、Jean-Jacques Vasseur、Anne Imberty、François Morvan

  DOI：10.1039/c3ra43807d

  日期：——

  their ability to bind to Burkholderia ambifaria Lectin (BambL). Binding evaluation was performed through inhibition of hemagglutination (HIA), surface plasmon resonance (SPR) and isothermal titration microcalorimetry (ITC). All fucosylated glycoclusters exhibited a higher affinity to BambL than methyl α-L-fucoside. A dissociation constant of 43 nM was observed for the fucocluster exhibiting four residues

  基于甘露糖中心和支链磷酸二酯支架，在两个不同的空间环境下合成了五个具有4、6或8个残基的岩藻糖基化糖簇。他们的合成是在溶液中使用亚磷酰胺化学方法生成磷酸二酯键并结合Cu（I）催化的叠氮化物-炔烃环加成反应（CuAAC）进行的。评估多价配体结合至冈比亚伯克霍尔德菌凝集素（BambL）的能力。通过抑制血凝（HIA），表面等离振子共振（SPR）和等温滴定微量热法（ITC）进行结合评估。所有岩藻糖基化糖簇均对BambL的亲和力高于甲基α- L-岩藻糖苷。对于表现出四个残基的岩藻簇，其支链磷酸二酯空间环境的解离常数为43 nM，与甲基α- L-岩藻糖苷相比增加了22倍。这些多价fucoclusters代表对BambL具有高亲和力的配体的第一个例子。