(2R,5S,6R)-5-azido-6-benzyloxyheptane-1,2-diol | 922490-88-8

• 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: (2R,5S,6R)-5-azido-6-benzyloxyheptane-1,2-diol
• CAS: 922490-88-8
• 化学式: C₁₄H₂₁N₃O₃
• 分子量: 279.339
• InChiKey: SKGDBQCGVJAFSC-BNOWGMLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  98.45
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,5S,6R)-5-azido-6-benzyloxyheptane-1,2-diol 在 四溴化碳 、 三苯基膦 作用下， 生成 ((2R,3S,6S)-6-Bromomethyl-2-methyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Characterization of Protein Encoded by spnR from the Spinosyn Gene Cluster of Saccharopolyspora spinosa:  Mechanistic Implications for Forosamine Biosynthesis

  摘要：

  d-Forosamine is a 4-N,N-(dimethylamino)-2,3,4,6-tetradeoxy-alpha-d-threo-hexopyranose found in spinosyn produced by Saccharopolyspora spinosa. Studies of spinosyn biosynthesis in S. spinosa led to the isolation of the entire biosynthetic gene cluster. Heterologous expression of spnR, one putative gene in forosamine biosynthesis, in E. coli and purification of the SpnR protein identified it as an aminotransferase catalyzing the conversion of the 4-keto-2,3,6-trideoxy sugar intermediate to the corresponding 4-amino sugar product. Identification of SpnR function relied on the use of a stable TMP-phosphonate sugar in place of TDP-sugar substrate to determine the function of SpnR. This strategy may find general applicability for designing probes to study enzymes which catalyze the transformation of labile deoxysugar intermediates.

  DOI：

  10.1021/ja042702k
• 作为产物：
  描述：

  (R)-2-benzyloxypropanal 在 偶氮二甲酸二异丙酯 、 AD-mix-β 、 二苯基磷酸 、 三苯基膦 作用下， 以 乙醚 为溶剂， 生成 (2R,5S,6R)-5-azido-6-benzyloxyheptane-1,2-diol
  参考文献：
  名称：

  Characterization of Protein Encoded by spnR from the Spinosyn Gene Cluster of Saccharopolyspora spinosa:  Mechanistic Implications for Forosamine Biosynthesis

  摘要：

  d-Forosamine is a 4-N,N-(dimethylamino)-2,3,4,6-tetradeoxy-alpha-d-threo-hexopyranose found in spinosyn produced by Saccharopolyspora spinosa. Studies of spinosyn biosynthesis in S. spinosa led to the isolation of the entire biosynthetic gene cluster. Heterologous expression of spnR, one putative gene in forosamine biosynthesis, in E. coli and purification of the SpnR protein identified it as an aminotransferase catalyzing the conversion of the 4-keto-2,3,6-trideoxy sugar intermediate to the corresponding 4-amino sugar product. Identification of SpnR function relied on the use of a stable TMP-phosphonate sugar in place of TDP-sugar substrate to determine the function of SpnR. This strategy may find general applicability for designing probes to study enzymes which catalyze the transformation of labile deoxysugar intermediates.

  DOI：

  10.1021/ja042702k

文献信息

• <i>In Vitro</i> Characterization of the Enzymes Involved in TDP-<scp>d</scp>-Forosamine Biosynthesis in the Spinosyn Pathway of <i>Saccharopolyspora </i><i>spinosa</i>
  作者：Lin Hong、Zongbao Zhao、Charles E. Melançon、Hua Zhang、Hung-wen Liu

  DOI：10.1021/ja0771383

  日期：2008.4.1

  6-tetradeoxy-beta-D-threo-hexopyranose) is a highly deoxygenated sugar component of several important natural products, including the potent yet environmentally benign insecticide spinosyns. To study D-forosamine biosynthesis, the five genes (spnO, N, Q, R, and S) from the spinosyn gene cluster thought to be involved in the conversion of TDP-4-keto-6-deoxy-D-glucose to TDP-D-forosamine were cloned and heterologously

  Forosamine (4-二甲氨基)-2,3,4,6-tetradeoxy-beta-D-threo-hexopyranose) 是几种重要天然产物的高度脱氧糖成分，包括强效但对环境无害的杀虫剂多杀菌素。为了研究 D-forosamine 生物合成，来自多杀菌素基因簇的五个基因（spnO、N、Q、R 和 S）被认为参与了 TDP-4-keto-6-deoxy-D-葡萄糖向 TDP 的转化-D-forosamine 被克隆并异源表达，相应的蛋白质被纯化并在体外检查它们的活性。先前的工作表明，SpnQ 作为一种依赖于 5'-单磷酸酯 (PMP) 的 3-脱水酶，在细胞还原酶对铁氧还蛋白/铁氧还蛋白还原酶或黄素氧还蛋白/黄素氧还蛋白还原酶存在的情况下，催化 TDP-4 的 C-3 脱氧-keto-2,6-dideoxy-D-葡萄糖。还确定 SpnR 作为转氨酶发挥作用，将 SpnQ 产物 TDP-4-keto-2