[(E)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enyl] phosphono hydrogen phosphate | 1356821-48-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(E)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enyl] phosphono hydrogen phosphate
• CAS: 1356821-48-1
• 化学式: C₁₁H₂₂O₁₃P₂
• 分子量: 424.235
• InChiKey: IQWLQHBLPMHJEB-ZCIPGPJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  213
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  4-hydroxy-prenyl tert-butyldimethylsilyl ether 在 ammonium hydroxide 、 N-氯代丁二酰亚胺 、 二甲基硫 、 四丁基氟化铵 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 、 silver carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 35.08h， 生成 [(E)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybut-2-enyl] phosphono hydrogen phosphate
  参考文献：
  名称：

  Synthesis and immunological evaluation of the 4-β-glucoside of HMBPP

  摘要：

  HMBPP ((E)-4-hydroxy-3-methyl-2-butenyl pyrophosphate) is a highly potent innate immunogen that stimulates human gamma delta T cells expressing the V gamma 2V delta 2 T cell antigen receptor. To determine if glycoside conjugates of HMBPP retain activity, the 4-beta-glucoside and its acetylated homolog were synthesized and tested for their ability to stimulate gamma delta T cells. The glycoside HMBPP conjugate stimulated human gamma delta T cells with an EC50 of 78 nM. The tetraacetyl glycoside HMBPP conjugate was also active (EC50 = 360 nM). The two isomeric mono-beta-glucosides of the parent (E)-2-methylbut-2-ene-1,4-diol, however, were not active. Thus, HMBPP glycosylated at the 4-OH position stimulates gamma delta T cells as long as the pyrophosphate moiety is present. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.055

文献信息

• Synthesis and immunological evaluation of the 4-β-glucoside of HMBPP
  作者：José-Luis Giner、Hong Wang、Craig T. Morita

  DOI：10.1016/j.bmcl.2011.12.055

  日期：2012.1

  HMBPP ((E)-4-hydroxy-3-methyl-2-butenyl pyrophosphate) is a highly potent innate immunogen that stimulates human gamma delta T cells expressing the V gamma 2V delta 2 T cell antigen receptor. To determine if glycoside conjugates of HMBPP retain activity, the 4-beta-glucoside and its acetylated homolog were synthesized and tested for their ability to stimulate gamma delta T cells. The glycoside HMBPP conjugate stimulated human gamma delta T cells with an EC50 of 78 nM. The tetraacetyl glycoside HMBPP conjugate was also active (EC50 = 360 nM). The two isomeric mono-beta-glucosides of the parent (E)-2-methylbut-2-ene-1,4-diol, however, were not active. Thus, HMBPP glycosylated at the 4-OH position stimulates gamma delta T cells as long as the pyrophosphate moiety is present. (C) 2011 Elsevier Ltd. All rights reserved.