2-cyanoethyl-[5'-O-(2',3'-di-O-acetyl)adenosine]-N,N-diisopropylaminophosphine | 303053-36-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-cyanoethyl-[5'-O-(2',3'-di-O-acetyl)adenosine]-N,N-diisopropylaminophosphine
• 英文别名: N(iPr)2P(OCH2CH2CN)(-5)Ribf2Ac3Ac(b)-adenin-9-yl；[(2R,3R,4R,5R)-4-acetyloxy-5-(6-aminopurin-9-yl)-2-[[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxymethyl]oxolan-3-yl] acetate
• CAS: 303053-36-3
• 化学式: C₂₃H₃₄N₇O₇P
• 分子量: 551.539
• InChiKey: GFIIFFRDQFOLJE-GPGNLKGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl-[5'-O-(2',3'-di-O-acetyl)adenosine]-N,N-diisopropylaminophosphine 在 四氮唑 、 硼烷-二异丙胺 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of a boron analogue of glucose-conjugated nucleoside diphosphate: nucleoside α-P-boranodiphosphoglucose

  摘要：

  Analogues of nucleoside diphosphohexoses are useful for investigating the role of nucleotidyl sugars in oligosaccharide metabolism. Here, adenosine alpha-P-boranodiphosphoglucose 4, a boron analogue of ADP-glucose in which borane (BH3) replaces the non-bridging oxygen of the phosphate, was prepared in good yield. The two diastereomers (4a and 4b) were successfully separated by reverse phase HPLC, and the chemical structures of isomers 4a and 4b were established via spectroscopic methods. The analogue may be useful for investigations of the stereochemistry and mechanism of enzymes such as glycogen and starch synthetases, glycosidyl and nucleosidyl transferases, kinases, etc. The described method may be used to prepare other boronated nucleotidyl sugar analogues for potential therapeutic applications and delivery of boron into cells for boron neutron capture therapy. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01141-2
• 作为产物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 2,3-二乙酸腺苷酸酯 在 二异丙基铵盐四氮唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-cyanoethyl-[5'-O-(2',3'-di-O-acetyl)adenosine]-N,N-diisopropylaminophosphine
  参考文献：
  名称：

  含硼 ADP 和 GDP 类似物的合成：核苷 5'-(P-硼酸二磷酸盐)

  摘要：

  以高产率合成了天然存在的二磷酸核苷 ADP 和 GDP 的新 5'-(Pα-硼化) 类似物，即腺苷 5'-(Pα-硼酸二磷酸) (ADPαB; 5a) 和鸟苷 5'-(Pα-硼酸二磷酸) ) (GDPαB; 5b)。通过反相高效液相色谱法成功分离了它们的非对映异构体，并通过光谱方法建立了化学结构。用硼烷 (BH3) 等电子取代磷酸二酯中的一个非桥接 O 原子应该会增加 ADPαB 和 GDPαB 的亲脂性和极性变化。硼化核苷二磷酸可用于研究涉及 ADP 和 GDP 的酶促反应的立体化学过程和金属需求，并作为 10B 的载体用于治疗癌症的硼中子俘获疗法 (BNCT)。

  DOI：

  10.1002/1522-2675(20000705)83:7<1392::aid-hlca1392>3.0.co;2-h

文献信息

• Method for the treatment of dental caries caused by streptococci mutans infection by inhibiting energy storage and utilization
  申请人：Pyro Pharmaceuticals, Inc.

  公开号：US20030232021A1

  公开（公告）日：2003-12-18

  A method and pharmaceutical composition for inhibiting infections of S. mutans by the addition of said composition to toothpaste or mouthwash, by inhibiting the production of ADP-glucose, particularly by inhibiting the activity of ADP-glucose pyrophosphorylase or glycogen synthase.

  一种方法和药物组成物，通过将所述组成物添加到牙膏或漱口水中，通过抑制ADP葡萄糖的生产，特别是通过抑制ADP葡萄糖焦磷酸化酶或糖原合成酶的活性，从而抑制S. mutans的感染。
• Synthesis of C-glycosidically linked ADP glycero-β-d-manno-heptose analogues
  作者：Andrea Graziani、Hassan Amer、Alla Zamyatina、Andreas Hofinger、Paul Kosma

  DOI：10.1016/j.tetasy.2006.12.015

  日期：2007.1

  C-Glycosides Of L-glycero-D-manno- and D-glycero-D-manno-heptose containing either (S)- or (R)-2-hydroxypropyl aglycons are easily accessible compounds via condensation of reducing heptoses with pentane-2,4-dione. 2%3'-Di-O-acetyl adenosine was transformed into the corresponding 5'-O-cyanoethyl N,N-diisopropylaminophosphoramidite derivative, which was coupled in fair yields to the O-acetylated diastereoisomeric C-glycosidic alcohols. Oxidation of the phosphite triesters followed by deprotection furnished four ADP-heptose analogues, wherein the heptosyl phosphate moiety had been replaced by a three carbon-skeleton. The compounds serving as substrate analogues will be used for co-crystallization experiments with ADP heptosyl transferases. (c) 2007 Elsevier Ltd. All rights reserved.