5-<2H>-D-glucose | 136864-16-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-<2H>-D-glucose
• 英文别名: D-Glucose-d1-1；(2R,3S,4R,5R)-5-deuterio-2,3,4,5,6-pentahydroxyhexanal
• CAS: 136864-16-9
• 化学式: C₆H₁₂O₆
• 分子量: 181.15
• InChiKey: GZCGUPFRVQAUEE-SPRLRUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-O-benzyl-6-O-triphenylmethyl-1,2-O-isopropylidene-5-(2H)-D-glucofuranoside 以64%的产率得到5-<2H>-D-glucose
  参考文献：
  名称：

  Glucose is a Precursor of 1-deoxynojirimycin and 1-deoxymannonojirimycin in Streptomyces subrutilus

  摘要：

  Streptomyces subrutilus ATCC 27467, when grown on a glucose-containing soyabean medium, produces both 1-deoxymannonojirimycin (DMJ) and 1-deoxynojirimycin (DNJ) in its culture medium. When 1- or 2-[H-2]-D-glucose is used, the deuterium label appears at C6 in both alkaloids and the labelling pattern suggests that the first step in the biosynthesis of both DNJ and DMJ is a glucose to fructose isomerisation. Studies with 5-[H-2]- and 6,6-[H-2(2)]-D-glucose indicate that oxidation of the 6-position of the glucose/fructose occurs during the biosynthesis and that mannonojirimycin is the first aminosugar to be formed. Mannonojirimycin can then undergo dehydration and reduction to DMJ. Alternatively, epimerisation of mannonojirimycin can occur at C2 to give norjirimycin which is then dehydrated and reduced to DNJ.

  DOI：

  10.1016/s0040-4020(01)88220-x