benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-(((bis(benzyloxy)phosphoryl)oxy)methyl)cyclohexyl)carbamate | 1316231-13-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-(((bis(benzyloxy)phosphoryl)oxy)methyl)cyclohexyl)carbamate
• CAS: 1316231-13-6
• 化学式: C₅₀H₅₂NO₉P
• 分子量: 841.938
• InChiKey: RVZBRNXKEKKXAX-WXOBWUEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.62
• 重原子数：
  61.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  110.78
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-(((bis(benzyloxy)phosphoryl)oxy)methyl)cyclohexyl)carbamate 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 20.0h， 以70%的产率得到validamine 7-phosphate
  参考文献：
  名称：

  Pseudoglycosyltransferase Catalyzes Nonglycosidic C–N Coupling in Validamycin A Biosynthesis

  摘要：

  Glycosyltransferases are ubiquitous in nature. They catalyze a glycosidic bond formation between sugar donors and sugar or nonsugar acceptors to produce oligo/polysaccharides, glycoproteins, glycolipids, glycosylated natural products, and other sugar-containing entities. However, a trehalose 6-phosphate synthase-like protein has been found to catalyze an unprecedented nonglycosidic C-N bond formation in the biosynthesis of the aminocyclitol antibiotic validamycin A. This dedicated 'pseudoglycosyltransferase' catalyzes a condensation between GDP-valienol and validamine 7-phosphate to give validoxylamine A 7'-phosphate with net retention of the 'anomeric' configuration of the donor cyclitol in the product. The enzyme operates in sequence with a phosphatase, which dephosphorylates validoxylamine A 7'-phosphate to validoxylamine A.

  DOI：

  10.1021/ja203574u
• 作为产物：
  描述：

  benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate 在 四氮唑 、 sodium methylate 、 溶剂黄146 、 间氯过氧苯甲酸 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.17h， 生成 benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-(((bis(benzyloxy)phosphoryl)oxy)methyl)cyclohexyl)carbamate
  参考文献：
  名称：

  Pseudoglycosyltransferase Catalyzes Nonglycosidic C–N Coupling in Validamycin A Biosynthesis

  摘要：

  Glycosyltransferases are ubiquitous in nature. They catalyze a glycosidic bond formation between sugar donors and sugar or nonsugar acceptors to produce oligo/polysaccharides, glycoproteins, glycolipids, glycosylated natural products, and other sugar-containing entities. However, a trehalose 6-phosphate synthase-like protein has been found to catalyze an unprecedented nonglycosidic C-N bond formation in the biosynthesis of the aminocyclitol antibiotic validamycin A. This dedicated 'pseudoglycosyltransferase' catalyzes a condensation between GDP-valienol and validamine 7-phosphate to give validoxylamine A 7'-phosphate with net retention of the 'anomeric' configuration of the donor cyclitol in the product. The enzyme operates in sequence with a phosphatase, which dephosphorylates validoxylamine A 7'-phosphate to validoxylamine A.

  DOI：

  10.1021/ja203574u