5'-deoxyinosine | 69655-07-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-deoxyinosine
• 英文别名: 5'-Deoxyinosine；9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-1H-purin-6-one
• CAS: 69655-07-8
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: IPJDTNIZLKTLEU-KQYNXXCUSA-N

物化性质

• 熔点：
  188-190 °C(Solv: methanol (67-56-1))
• 沸点：
  706.2±60.0 °C(Predicted)
• 密度：
  1.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-deoxyinosine 生成 [(2S,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl] dihydrogen phosphate
  参考文献：
  名称：

  NAKANO, KATSUYUKI;YASAKA, TOSHIO;SCHRAM, KARL H.;REIMER, MARK L. J.;MCCLU+, J. CHROMATOGR., 515,(1990) C. 537-546

  摘要：

  DOI：
• 作为产物：
  描述：

  5'-氯-5'-脱氧腺苷 在 adenylate deaminase 、 三乙基硼氢化锂 、 二甲基亚砜 作用下， 以 phosphate buffer 、 二甲基亚砜 为溶剂， 反应 0.17h， 生成 5'-deoxyinosine
  参考文献：
  名称：

  腺苷酸脱氨酶（5'-腺苷酸脱氨酶，AMPDA）-催化 5'-脱氧-5'-取代和 5'-保护的腺苷脱氨：与腺苷脱氨酶 (ADA) 催化活性的比较

  摘要：

  腺苷酸脱氨酶 (AMPDA) 能够催化 5'-取代和 5'-保护的 5'-脱氧腺苷的水解脱氨，而腺苷脱氨酶 (ADA) 对相同底物的活性有限或没有活性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300435

文献信息

• 一种1,2,3-三-O-乙酰基-5-脱氧-β-D-核糖 的制备方法
  申请人：新乡拓新药业股份有限公司

  公开号：CN107827938B

  公开（公告）日：2020-08-07

  本发明公开了一种1,2,3‑三‑O‑乙酰基‑5‑脱氧‑β‑D‑核糖的制备方法，属于核苷药物合成领域。其反应步骤如下：以肌苷为原料，与有机硼酸反应，对2′和3′羟基进行保护，随后在硼氢化钾和三氟乙酸条件下室温还原，随后二醇交换脱保护，最后加入醋酐回流反应得到1,2,3‑三‑O‑乙酰基‑5‑脱氧‑β‑D‑核糖。本合成方法原料易得，步骤短，工艺安全性高，具有工业化应用前景。
• [EN] ADENOSINE KINASE INHIBITORS
  申请人：GENSIA, INC.

  公开号：WO1992012718A1

  公开（公告）日：1992-08-06

  (EN) Novel compounds which selectively inhibit adenosine kinase and methods of preparing adenosine kinase inhibitors are provided. Also provided are methods of treating various conditions which may be ameliorated by increased local concentrations of adenosine using adenosine kinase inhibitors.(FR) L'invention se rapporte à de nouveaux composés qui possèdent un pouvoir inhibiteur sélectif sur l'adénosine-kinase, ainsi qu'à des procédés de préparation d'agents inhibiteurs de l'adénosine-kinase. Sont également décrits des procédés qui servent à traiter divers états dont on peut obtenir une amélioration en augmentant les concentrations locales d'adénosine et qui utilisent à cet effet des agents inhibiteurs de l'adénosine-kinase.

  提供了一种新型化合物，可选择性地抑制腺苷激酶，并提供制备腺苷激酶抑制剂的方法。还提供了使用腺苷激酶抑制剂治疗可能通过增加局部腺苷浓度改善的各种情况的方法。
• ——
  作者：Lisam Singh、Ramesh Sharma

  DOI：10.1023/a:1007087905192

  日期：——

  initial ADA activity. In addition, various purine analogs such as inosine, purine, alpha-adenosine and adenine showed variable inhibitions on the activity of ADA. Relative ADA activity towards 3'-deoxyadenosine and 6-chloropurine riboside was lower by 30% and 40%, respectively. However, the activity towards 2'-o-methyl adenosine was higher (30%) compared to the activity obtained using adenosine.

  从小鼠小肠中分离出腺苷脱氨酶（ADA），并纯化至最大同质性。纯化的ADA的SDS-PAGE给出分子量为41kDa。蛋白质印迹分析给出了一个41 kDa的反应带，另一个是相关的ADA结合蛋白。纯化的酶在碱性pH下更稳定。最佳pH和pI值分别约为7.0和4.96。小肠腺苷和2'-脱氧腺苷的Km值分别为23和16 microM。嘌呤核糖苷是竞争性抑制剂，Ki为5 microM，而2'-3'-o-异亚丙基腺苷则作为竞争性抑制剂（Ki 66 microM）。茶碱（-40％），咖啡因（-30％）和L-半胱氨酸（-50％）的存在抑制了ADA的活性。重要的是 Hg2 +（100 microM）抑制了ADA初始活性的98％。另外，各种嘌呤类似物，如肌苷，嘌呤，α-腺苷和腺嘌呤显示出对ADA活性的可变抑制。相对于3'-脱氧腺苷和6-氯嘌呤核糖核苷的相对ADA活性分别降低了30％和40％。但是，与使用腺苷获得的
• Compositions and methods of modulating the immune response by activating alpha protein kinase 1
  申请人：Shanghai Yao Yuan Biotechnology Co., Ltd.

  公开号：US11149051B2

  公开（公告）日：2021-10-19

  The disclosure provides compositions and methods related to activating alpha-kinase 1 (ALPK1) for modulating an immune response and treating or preventing cancer, infection, inflammation and related diseases and disorders as well as potentiating an immune response to a target antigen. The disclosure also provides heterocyclic compounds of formula (I) as agonists of alpha protein kinase 1 (ALPK1) and their use in activating ALPK1, modulating an immune response and treating diseases such as cancer, wherein A1, A2, L1, L2, L3, Z1, Z2, W1, W2, R1, R2, R3, R4, R5, R6 and R7 are defined herein.

  本公开提供了与激活α蛋白激酶1（ALPK1）有关的组合物和方法，用于调节免疫反应和治疗或预防癌症、感染、炎症及相关疾病和失调，以及增强对靶抗原的免疫反应。本公开还提供了作为α蛋白激酶1（ALPK1）激动剂的式(I)杂环化合物及其在激活ALPK1、调节免疫应答和治疗癌症等疾病中的用途，其中A1、A2、L1、L2、L3、Z1、Z2、W1、W2、R1、R2、R3、R4、R5、R6和R7在本文中定义。
• Deamination of 6-Aminodeoxyfutalosine in Menaquinone Biosynthesis by Distantly Related Enzymes
  作者：Alissa M. Goble、Rafael Toro、Xu Li、Argentina Ornelas、Hao Fan、Subramaniam Eswaramoorthy、Yury Patskovsky、Brandan Hillerich、Ron Seidel、Andrej Sali、Brian K. Shoichet、Steven C. Almo、Subramanyam Swaminathan、Martin E. Tanner、Frank M. Raushel

  DOI：10.1021/bi400750a

  日期：2013.9.17

  Proteins of unknown function belonging to cog1816 and cog0402 were characterized. Sav2595 from Steptomyces avermitilis MA-4680, Ace10264 from Acidothermus cellulolyticus 11B, Nis0429 from Nitratiruptor sp. SB155-2 and Dr0824 from Deinococcus radiodurans R1 were cloned, purified, and their substrate profiles determined. These enzymes were previously incorrectly annotated as adenosine deaminases or chlorohydrolases. It was shown here that these enzymes actually deaminate 6-aminodeoxyfutalosine. The deamination of 6-aminodeoxyfutalosine is part of an alternative menaquinone biosynthetic pathway that involves the formation of futalosine. 6-Aminodeoxyfutalosine is deaminated by these enzymes with catalytic efficiencies greater than 106 M-1 s(-1), Km values of 0.9-6.0 mu M, and k(cat) values of 1.2-8.6 Adenosine, 2'-deoxyadenosine, thiomethyladenosine, and S-adenosylhomocysteine are deaminated at least an order of magnitude slower than 6-aminodeoxyfutalosine. The crystal structure of Nis0429 was determined and the substrate, 6-aminodeoxyfutalosine, was positioned in the active site on the basis of the presence of adventitiously bound benzoic acid. In this model, Ser-145 interacts with the carboxylate moiety of the substrate. The structure of.Dr0824 was also determined, but a collapsed active site pocket prevented docking of substrates. A computational model of Sav2595 was built on the basis of the crystal structure of adenosine deaminase and substrates were docked. The model predicted a conserved arginine after beta-strand 1 to be partially responsible for the substrate specificity of Sav2595.