Adenosine monosuccinate | 102029-71-0

• 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: Adenosine monosuccinate
• 英文别名: 5'-Succinyladenosine；4-{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}-4-oxobutanoic acid；adenosine 5'-succinate；succinic acid mono-adenosin-5'-yl ester；Bernsteinsaeure-mono-adenosin-5'-ylester；4-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy]-4-oxobutanoic acid
• CAS: 102029-71-0
• 化学式: C₁₄H₁₇N₅O₇
• 分子量: 367.318
• InChiKey: SOVSEJILHKLDOS-UISLRAPISA-N

物化性质

• 沸点：
  773.4±70.0 °C(Predicted)
• 密度：
  1.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  183
• 氢给体数：
  4
• 氢受体数：
  11

制备方法与用途

生物活性

腺苷-5'-琥珀酸（Adenosine 5'-succinate）是一种与AMP在化学结构上相关的化合物，能够有效抑制转导蛋白对Denatonium benzoate/味觉受体的激活。

体外研究

Adenosine 5'-succinate (5.0 mM) 剂量下能强烈抑制Denatonium benzoate（DEN）/味觉受体对转导蛋白的激活。Adenosine 5'-succinate可能与苦味响应性味觉受体结合，作为一种天然的味觉调节剂。

反应信息

• 作为产物：
  描述：

  4-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-4-oxobutanoic acid 在 三氟乙酸 作用下， 反应 48.0h， 以53%的产率得到Adenosine monosuccinate
  参考文献：
  名称：

  Potential utility of adenosine 5′-ester prodrugs to enhance its plasma half-life: synthesis and molecular docking studies

  摘要：

  Adenosine, the adenine nucleoside, has demonstrated various pharmacological properties related to the treatment of relevant clinical diseases. With respect to this, one of the most fascinating biological activities of adenosine is its capacity for reversing hepatic fibrosis, which has been established in several in vitro and in vivo studies. Although adenosine seems to be a privileged compound, it lacks of metabolic stability to be considered as a drug candidate. For this reason, in this preliminary study, six prodrugs were developed in order to enhance the plasma half-life of adenosine, in which the esterification at 5' position of adenosine was considered. According to previous works, the increase in steric hindrance at this position could develop unfavorable interactions inside adenosine deaminase (ADA) catalytic domain, which is reported as the main enzyme implicated in adenosine metabolism. Besides, molecular docking was employed to verify if the hindrance at carbinol group in the prodrugs is enough to diminish its oxidation and also to predict if compounds would be metabolized by a promiscuous esterase. Finally, the in vitro assays corroborated the theoretical findings and also indicated that the compounds are less metabolized than adenosine by ADA; in the case of compounds containing proline and thioproline progroups (4d and 4e, respectively), the reduction was more than three-fold of decrease.

  DOI：

  10.1007/s00044-014-1299-z

文献信息

• Alkyl-linked nucleotide compositions
  申请人：Serenex, Inc.

  公开号：US20040215009A1

  公开（公告）日：2004-10-28

  Alkyl-linked nucleotide compositions and nucleotide affinity media comprising an alkyl-linked nucleotide are provided. The linker is generally a hydrophobic linker that can be a 3, 4, 5, 6, 7, 8, 9, 10, or a longer carbon chain. Also included in the invention are methods for synthesis of an alkyl-linked nucleotide, nucleotide affinity media and methods of use thereof for affinity chromatography and screening methods.

  本发明提供了含有烷基连接的核苷酸组成物和包含烷基连接的核苷酸的核苷酸亲和介质。连接剂通常是一个疏水性连接剂，可以是3、4、5、6、7、8、9、10或更长的碳链。本发明还包括合成烷基连接的核苷酸、核苷酸亲和介质以及用于亲和色谱和筛选方法的使用方法。
• Taste masking product
  申请人：The University of Western Australia

  公开号：US11331268B2

  公开（公告）日：2022-05-17

  This invention relates to a chocolate or chocolate substitute composition or product comprising (a) at least compound to be delivered to a subject; (b) a chocolate or chocolate substitute matrix and at least (i) a masking agent or (ii) a firming agent, wherein the composition or product is substantially stable.

  本发明涉及一种巧克力或巧克力替代物组合物或产品，它包含：(a) 至少一种要输送给受试者的化合物；(b) 一种巧克力或巧克力替代物基质和至少(i) 一种掩蔽剂或(ii) 一种紧固剂，其中组合物或产品基本稳定。
• Synthesis and structure-activity relationships of adenosine analogs as inhibitors of trypanosomal glyceraldehyde-3-phosphate dehydrogenase. Modifications at positions 5′ and 8
  作者：Alex M. Aronov、Michael H. Gelb

  DOI：10.1016/s0960-894x(98)00635-0

  日期：1998.12

  A number of 5', N6- and C8, N6-disubstituted adenosine analogs was synthesized and tested for inhibition of trypanosomal glyceraldehyde 3-phosphate dehydrogenase. The most active compound, N6-(3-methyl-2-butenyl)-8-(2-thienyl)adenosine, had Kl of 9 microM and was marginally selective for the parasite enzyme.
• Huber, Chemische Berichte, 1956, vol. 89, p. 2853,2857
  作者：Huber

  DOI：——

  日期：——
• TREATMENT OF TOXOPLASMOSIS
  申请人：UNIVERSITY OF ALABAMA, BIRMINGHAM RESEARCH FOUNDATION

  公开号：EP0755255A1

  公开（公告）日：1997-01-29