adenosine 5'-(trihydrogen diphosphate) 3'-(dihydrogen phosphate) 5'-<(R)-3-hydroxy-4-<<3-(propylamino)-3-oxopropyl>thio>-2,2-dimethyl-4-oxobutyl> ester | 223710-76-7

• 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: adenosine 5'-(trihydrogen diphosphate) 3'-(dihydrogen phosphate) 5'-<(R)-3-hydroxy-4-<<3-(propylamino)-3-oxopropyl>thio>-2,2-dimethyl-4-oxobutyl> ester
• 英文别名: S-[3-oxo-3-(propylamino)propyl] (2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanethioate
• CAS: 223710-76-7
• 化学式: C₂₂H₃₇N₆O₁₆P₃S
• 分子量: 766.554
• InChiKey: ADBSJOZLOIFJIW-MAECAPAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  360
• 氢给体数：
  8
• 氢受体数：
  21

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
  ——	adenosine 5'-(trihydrogen diphosphate) 3'-(dihydrogen phosphate) 5'-<(R)-3-hydroxy-4-<(6-mercaptohexyl)amino>-2,2-dimethyl-4-oxobutyl> ester	——	C22H39N6O15P3S	752.57
  ——	adenosine 5'-(trihydrogen diphosphate) 3'-(dihydrogen phosphate) 5'-<(R)-3-hydroxy-4-<<3-<2-(mercaptoethyl)amino>-3-oxobutyl>amino>-2,2-dimethyl-4-oxobutyl> ester	——	C22H38N7O16P3S	781.568
  ——	adenosine 5'-(trihydrogen diphosphate) 3'-(dihydrogen phosphate) 5'-<(R)-3-hydroxy-4-<(6-carboxyheptyl)amino>-2,2-dimethyl-4-oxobutyl> ester	——	C24H41N6O17P3	778.541

反应信息

• 作为反应物：
  描述：

  8-氨基辛酸 、 adenosine 5'-(trihydrogen diphosphate) 3'-(dihydrogen phosphate) 5'-<(R)-3-hydroxy-4-<<3-(propylamino)-3-oxopropyl>thio>-2,2-dimethyl-4-oxobutyl> ester 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 96.0h， 以20%的产率得到adenosine 5'-(trihydrogen diphosphate) 3'-(dihydrogen phosphate) 5'-<(R)-3-hydroxy-4-<(6-carboxyheptyl)amino>-2,2-dimethyl-4-oxobutyl> ester
  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 、 三甲基氯硅烷 、 pyrophosphatase 、 pyruvate kinase 、 dephosphocoenzyme A kinase 、 phospho(enol) pyruvate 、 phosphopantetheine adenylyltransferase 、 四丁基溴化铵 、 cesium fluoride 、 magnesium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 235.0h， 生成 adenosine 5'-(trihydrogen diphosphate) 3'-(dihydrogen phosphate) 5'-<(R)-3-hydroxy-4-<<3-(propylamino)-3-oxopropyl>thio>-2,2-dimethyl-4-oxobutyl> ester
  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.