1-O-[(3'R,4'S)-3-hydroxytetrahydrofuran-4-yl] β-D-xylopyranoside 3,4,3'-trisphosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-[(3'R,4'S)-3-hydroxytetrahydrofuran-4-yl] β-D-xylopyranoside 3,4,3'-trisphosphate
• 英文别名: [(3R,4S)-4-[(2S,3R,4R,5R)-3-hydroxy-4,5-diphosphonooxyoxan-2-yl]oxyoxolan-3-yl] dihydrogen phosphate
• 化学式: C₉H₁₉O₁₆P₃
• 分子量: 476.162
• InChiKey: LNNHGAKKYVKVBV-YQWDKWCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  248
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  D-吡喃木糖 在 palladium on activated charcoal 、 palladium dichloride 吡啶 、 四氮唑 、 盐酸 、 sodium hydroxide 、 氢气 、 silver perchlorate 、 sodium hydride 、 对甲苯磺酸 、 乙酰氯 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 氘代氯仿 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 66.33h， 生成 1-O-[(3'R,4'S)-3-hydroxytetrahydrofuran-4-yl] β-D-xylopyranoside 3,4,3'-trisphosphate
  参考文献：
  名称：

  Xylopyranoside-based agonists of d-myo-inositol 1,4,5-trisphosphate receptors: synthesis and effect of stereochemistry on biological activity

  摘要：

  The synthesis of a series of tetrahydrofuranyl alpha- and beta -xylopyranoside trisphosphates, designed by excision of three motifs of adenophostin A is reported. The synthetic route features improved preparations of allyl alpha -D-xylopyranoside and its 2-O-benzyl ether, and gives access to four diastereoisomeric trisphosphates, which show a range of abilities to mobilise Ca2+ from the intracellular stores of hepatocytes. A comparison of the potencies of the four trisphosphates provides useful information relating to the effects of stereochemical variation on the recognition of carbohydrate-based trisphosphates by D-myo-inositol 1,4,5-trisphosphate receptors. 1-O-[(3 'S,4 'R)-3-hydroxytetrahydrofuran-4-yl] alpha -D-xylopyranoside 3,4,3 ' -trisphosphate (8) is the most active member of the series with a potency close to Ins(1,4,5)P-3; a beta -linked analogue, 1-O-[(3 'R,4 'S)-3-hydroxytetrahydrofuran-4-yl] beta -D-xylopranoside 3,4,3 ' -trisphosphate, is ca. 20-fold weaker than Ins(1,4,5)P-3, and the other compounds are much less active. While no compound attained a potency close to that of adenophostin A, we believe that 8 represents the minimal structure for potent Ca2+-releasing activity in this type of carbohydrate-based analogue. (C) 2001 Elsevier Science I,td. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00067-2

文献信息

• Xylopyranoside-based agonists of d-myo-inositol 1,4,5-trisphosphate receptors: synthesis and effect of stereochemistry on biological activity
  作者：Heidi J. Rosenberg、Andrew M. Riley、Rachel D. Marwood、Vanessa Correa、Colin W. Taylor、Barry V.L. Potter

  DOI：10.1016/s0008-6215(01)00067-2

  日期：2001.5

  The synthesis of a series of tetrahydrofuranyl alpha- and beta -xylopyranoside trisphosphates, designed by excision of three motifs of adenophostin A is reported. The synthetic route features improved preparations of allyl alpha -D-xylopyranoside and its 2-O-benzyl ether, and gives access to four diastereoisomeric trisphosphates, which show a range of abilities to mobilise Ca2+ from the intracellular stores of hepatocytes. A comparison of the potencies of the four trisphosphates provides useful information relating to the effects of stereochemical variation on the recognition of carbohydrate-based trisphosphates by D-myo-inositol 1,4,5-trisphosphate receptors. 1-O-[(3 'S,4 'R)-3-hydroxytetrahydrofuran-4-yl] alpha -D-xylopyranoside 3,4,3 ' -trisphosphate (8) is the most active member of the series with a potency close to Ins(1,4,5)P-3; a beta -linked analogue, 1-O-[(3 'R,4 'S)-3-hydroxytetrahydrofuran-4-yl] beta -D-xylopranoside 3,4,3 ' -trisphosphate, is ca. 20-fold weaker than Ins(1,4,5)P-3, and the other compounds are much less active. While no compound attained a potency close to that of adenophostin A, we believe that 8 represents the minimal structure for potent Ca2+-releasing activity in this type of carbohydrate-based analogue. (C) 2001 Elsevier Science I,td. All rights reserved.