α-D-xylose 1-phosphate, free acid | 25799-81-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: α-D-xylose 1-phosphate, free acid
• 英文别名: D-xylose-1-phosphate；α-D-xylopyranosyl phosphate, free acid；O¹-Phosphono-α-D-xylopyranose；alpha-D-Xylose 1-phosphate；[(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl] dihydrogen phosphate
• CAS: 25799-81-9
• 化学式: C₅H₁₁O₈P
• 分子量: 230.111
• InChiKey: ILXHFXFPPZGENN-KKQCNMDGSA-N

物化性质

• 沸点：
  541.6±60.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  三正丁胺 、 α-D-xylose 1-phosphate, free acid 在 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 uridine-5'-xylose-1'-tetraphosphate triethylammonium
  参考文献：
  名称：

  Pyrimidine Nucleotides with 4-Alkyloxyimino and Terminal Tetraphosphate δ-Ester Modifications as Selective Agonists of the P2Y₄ Receptor

  摘要：

  P2Y(2) and P2Y(4) receptors are G protein-coupled receptors, activated by UTP and dinudeoside tetraphosphates, which are difficult to distinguish pharmacologically for lack of potent and selective ligands. We structurally varied phosphate and uracil moieties in analogues of pyrimidine nucleoside 5'-triphosphates and 5'-tetraphosphate esters. P2Y(4) receptor potency in phospholipase C stimulation in transfected 1321N1 human astrocytoma cells was enhanced in N-4-alkyloxycytidine derivatives. OH groups on a terminal delta-glucose phosphoester of uridine 5'-tetraphosphate were inverted or substituted with H or F to probe H-bonding effects. N-4-(Phenylpropoxy)-CTP 16 (MRS4062), Up(4)-[1]3'-deoxy-3'-fluoroglucose 34 (MRS2927), and N-4-(phenylethoxy)-CTP 15 exhibit >= 10-fold selectivity for human P2Y(4) over P2Y(2) and P2Y(6) receptors (EC50 values 23, 62, and 73 nM, respectively). delta-3-Chlorophenyl phosphoester 21 of Up(4) activated P2Y(2) but not P2Y(4) receptor. Selected nucleotides tested for chemical and enzymatic stability were much more stable than UTP. Agonist docking at CXCR4-based P2Y(2) and P2Y(4) receptor models indicated greater steric tolerance of N-4-phenylpropoxy group at P2Y(4). Thus, distal structural changes modulate potency, selectivity, and stability of extended uridine tetraphosphate derivatives, and we report the first P2Y(4) receptor-selective agonists.

  DOI：

  10.1021/jm101591j
• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 silver orthophosphate 、 苯 作用下， 生成 α-D-xylose 1-phosphate, free acid
  参考文献：
  名称：

  Anomeric 1-Dicyclohexylammonium Phosphate Esters of D-Glucopyranose, D-Galactopyranose, D-Xylopyranose and L-Arabinopyranose¹

  摘要：

  DOI：

  10.1021/ja01575a062

文献信息

• Synthesis of Maltose-1-phosphate and D-Xylose-1-phosphate
  作者：W. R. Meagher、W. Z. Hassid

  DOI：10.1021/ja01215a003

  日期：1946.11
• Neufeld et al., Archives of Biochemistry, 1957, vol. 69, p. 602,612
  作者：Neufeld et al.

  DOI：——

  日期：——
• The Isomeric Xylopyranose Triacetates Produced by Solvolysis of 2,3,4-Tri-O-acetyl-α-D-xylopyranosyl Bromide¹
  作者：Naval J. Antia

  DOI：10.1021/ja01555a059

  日期：1958.11
• ENZYMATIC SYNTHESIS OF URIDINE DIPHOSPHATE XYLOSE AND URIDINE DIPHOSPHATE ARABINOSE
  作者：V. Ginsburg、E. F. Neufeld、W. Z. Hassid

  DOI：10.1073/pnas.42.6.333

  日期：1956.6