S-[3-oxo-3-(propylamino)propyl] (2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanethioate | 223710-78-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: S-[3-oxo-3-(propylamino)propyl] (2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanethioate
• CAS: 223710-78-9
• 化学式: C₂₂H₃₆N₆O₁₃P₂S
• 分子量: 686.574
• InChiKey: RFDWRGBSVQCBAG-MAECAPAWSA-N

物化性质

• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  313
• 氢给体数：
  7
• 氢受体数：
  18

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5’-三磷酸腺苷	ATP	56-65-5	C10H16N5O13P3	507.184

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5'-腺嘌呤核苷酸	5'-adenosine monophosphate	61-19-8	C10H14N5O7P	347.224

反应信息

• 作为反应物：
  描述：

  S-[3-oxo-3-(propylamino)propyl] (2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanethioate 在 Crotalus atrox venom nucleotide pyrophosphatase EC 3.6.1.9 、 potato acid phosphatase EC 3.1.3.2 作用下， 以 水 为溶剂， 反应 25.0h， 生成 D-(-)-泛酰内酯
  参考文献：
  名称：

  Development of a Second Generation Coenzyme A Analogue Synthon

  摘要：

  We have previously reported a general synthetic approach to analogues of coenzyme A (CoA) which involves enzymatic synthesis of a general CoA analogue synthon having a thioester linkage in place of the amide bond nearest the thiol group (Martin et al. J. Am. Chem. Sec. 1994, 116, 4660), We report here the synthesis of a second CoA analogue synthon 1c which has the amide bond more distant from the thiol group replaced with a thioester, This analogue was prepared by nonenzymatic synthesis of a racemic phosphopantetheine analogue followed by enzymatic conversion to the corresponding CoA analogue. Stereochemical analysis showed that the natural enantiomer of the phosphopantetheine analogue was selectively converted to product by the enzyme phosphopantetheine adenylyltansferase, yielding a product that possessed the desired stereoconfiguration. Reaction of the new synthon 1c with a primary amine results in amide bond formation to form the CoA analogue of interest. This new methodology provides access to an even broader array of CoA analogues modified in the beta-alanylcysteamine moiety, This has been demonstrated in the synthesis of an analogue having an extra methylene group in the beta-alanine moiety and two analogues in which the amide bond nearest the thiol group is replaced with a pair of methylene groups.

  DOI：

  10.1021/jo981758s
• 作为产物：
  描述：

  2,2-二甲基-3-羟基丙醛 在 吡啶 、 tetrafluoroboric acid 、 正丁基锂 、 pyrophosphatase 、 pyruvate kinase 、 dephosphocoenzyme A kinase 、 phospho(enol) pyruvate 、 phosphopantetheine adenylyltransferase 、 cesium fluoride 、 magnesium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 220.0h， 生成 S-[3-oxo-3-(propylamino)propyl] (2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanethioate
  参考文献：
  名称：

  Development of a Second Generation Coenzyme A Analogue Synthon

  摘要：

  We have previously reported a general synthetic approach to analogues of coenzyme A (CoA) which involves enzymatic synthesis of a general CoA analogue synthon having a thioester linkage in place of the amide bond nearest the thiol group (Martin et al. J. Am. Chem. Sec. 1994, 116, 4660), We report here the synthesis of a second CoA analogue synthon 1c which has the amide bond more distant from the thiol group replaced with a thioester, This analogue was prepared by nonenzymatic synthesis of a racemic phosphopantetheine analogue followed by enzymatic conversion to the corresponding CoA analogue. Stereochemical analysis showed that the natural enantiomer of the phosphopantetheine analogue was selectively converted to product by the enzyme phosphopantetheine adenylyltansferase, yielding a product that possessed the desired stereoconfiguration. Reaction of the new synthon 1c with a primary amine results in amide bond formation to form the CoA analogue of interest. This new methodology provides access to an even broader array of CoA analogues modified in the beta-alanylcysteamine moiety, This has been demonstrated in the synthesis of an analogue having an extra methylene group in the beta-alanine moiety and two analogues in which the amide bond nearest the thiol group is replaced with a pair of methylene groups.

  DOI：

  10.1021/jo981758s

文献信息

• Development of a Second Generation Coenzyme A Analogue Synthon
  作者：Richard T. Bibart、Kurt W. Vogel、Dale G. Drueckhammer

  DOI：10.1021/jo981758s

  日期：1999.4.1

  We have previously reported a general synthetic approach to analogues of coenzyme A (CoA) which involves enzymatic synthesis of a general CoA analogue synthon having a thioester linkage in place of the amide bond nearest the thiol group (Martin et al. J. Am. Chem. Sec. 1994, 116, 4660), We report here the synthesis of a second CoA analogue synthon 1c which has the amide bond more distant from the thiol group replaced with a thioester, This analogue was prepared by nonenzymatic synthesis of a racemic phosphopantetheine analogue followed by enzymatic conversion to the corresponding CoA analogue. Stereochemical analysis showed that the natural enantiomer of the phosphopantetheine analogue was selectively converted to product by the enzyme phosphopantetheine adenylyltansferase, yielding a product that possessed the desired stereoconfiguration. Reaction of the new synthon 1c with a primary amine results in amide bond formation to form the CoA analogue of interest. This new methodology provides access to an even broader array of CoA analogues modified in the beta-alanylcysteamine moiety, This has been demonstrated in the synthesis of an analogue having an extra methylene group in the beta-alanine moiety and two analogues in which the amide bond nearest the thiol group is replaced with a pair of methylene groups.