(2S)-2-[formyl(hydroxy)amino]-5-[(6-oxo-1,7-dihydropurin-8-yl)sulfanyl]pentanoic acid | 1118887-67-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-[formyl(hydroxy)amino]-5-[(6-oxo-1,7-dihydropurin-8-yl)sulfanyl]pentanoic acid
• CAS: 1118887-67-4
• 化学式: C₁₁H₁₃N₅O₅S
• 分子量: 327.321
• InChiKey: DQHZKTHWNDBKHQ-LURJTMIESA-N

物化性质

• 沸点：
  736.5±70.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  173
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  benzyl (S)-2-(N-(benzyloxy)formamido)-5-((6-hydroxy-9H-purin-8-yl)thio)pentanoate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到(2S)-2-[formyl(hydroxy)amino]-5-[(6-oxo-1,7-dihydropurin-8-yl)sulfanyl]pentanoic acid
  参考文献：
  名称：

  Synthesis of 5-(6-hydroxy-7H-purine-8-ylthio)- 2-(N-hydroxyformamido)pentanoic acid

  摘要：

  我们已经开发了一种合成路线，用于制备基于核苷酸的混合双底物小分子。设计了一个原型化合物，并将其对接到AdSS酶的催化域中，将蛋白质的镁中心与核苷酸区域之间的区域连接起来。合成涉及将一种能够络合镁的溴化肽片段与一种硫化核苷酸偶合，以获得混合模型化合物。

  DOI：

  10.3762/bjoc.6.93

文献信息

• [EN] BISUBSTRATE INHIBITORS OF ADENYLOSUCCINATE SYNTHETASE<br/>[FR] INHIBITEURS À DEUX SUBSTRATS D'ADÉNYLOSUCCINATE SYNTHÉTASE
  申请人：UNIV CALIFORNIA

  公开号：WO2009023495A2

  公开（公告）日：2009-02-19

  The present invention provides compound having the general structure (A) or pharmaceutically acceptable salts thereof: (A) wherein each of R1 and R2 can be, independently, any one of-H, a halogen, -NH2, -OH, - NH-R3, and -O-R3; each of G1, G2, and G4, can be, independently any of CH, N, O, and S; G3 can be any Of CH2, NH, O; and S; or G3 and/or G4 can be C=O; G5 can be any of C and N; L can be absent or be any of O, NH, and S; R3 can be any of-H, an C1-C18 alkyl, an aryl,- C(O)-H, and -C(O)-alkyl; R4 can be any of -H, -C(O)O-; and -C(O)-R3; R5 can be any of - H, an C1 -C18 alkyl, or an aryl; M can be absent or be any Of -CH2-; -NH-; -NH-C(O)-; -O-, and -S-; and n is an integer having the value between 1 and 6. The compounds having the general structure A can serve as inhibitors of adenylosuccinate synthetase.
• Synthesis of 5-(6-hydroxy-7<i>H</i>-purine-8-ylthio)- 2-(<i>N</i>-hydroxyformamido)pentanoic acid
  作者：Yanmei Zhang、Greg Elliot、Adrian Saldanha、Igor Tsigelny、Dennis Carson、Wolf Wrasidlo

  DOI：10.3762/bjoc.6.93

  日期：——

  We have developed a synthetic route for the preparation of a hybrid bisubstrate small molecule based on a nucleoside. A prototype compound was designed and docked into the catalytic domain of the AdSS enzyme bridging the region between the magnesium center of the protein to the nucleoside region. The synthesis involves coupling a brominated peptide fragment capable of complexing magnesium to a thiolated nucleoside to obtain the hybrid model compound.

  我们已经开发了一种合成路线，用于制备基于核苷酸的混合双底物小分子。设计了一个原型化合物，并将其对接到AdSS酶的催化域中，将蛋白质的镁中心与核苷酸区域之间的区域连接起来。合成涉及将一种能够络合镁的溴化肽片段与一种硫化核苷酸偶合，以获得混合模型化合物。