6,7-dideoxy-1,2:3,5-di-O-isopropylidene-6-C-methyl-α-D-gluco-hept-6-enofuranose | 257613-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,7-dideoxy-1,2:3,5-di-O-isopropylidene-6-C-methyl-α-D-gluco-hept-6-enofuranose
• 英文别名: (1S,2R,6R,8R,9R)-4,4,11,11-tetramethyl-9-prop-1-en-2-yl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecane
• CAS: 257613-55-1
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: BAYXSCZFVYPSPZ-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-dideoxy-1,2:3,5-di-O-isopropylidene-6-C-methyl-α-D-gluco-hept-6-enofuranose 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 以97%的产率得到6,7-dideoxy-6-C-methyl-D-gluco-hept-6-enopyranose
  参考文献：
  名称：

  UDP-Glucose Analogues as Inhibitors and Mechanistic Probes of UDP-Glucose Dehydrogenase

  摘要：

  UDP-glucose dehydrogenase catalyzes the NAD(+)-dependent 2-fold oxidation of UDP-glucose to give UDP-glucuronic acid. The putative aldehyde intermediate is not released from the active site and is presumably tightly bound. We have prepared UDP-7-deoxy-alpha-D-gluco-hept-6-ulopyranose 5, that contains a methyl ketone at C-6 and cannot be further oxidized by the enzyme. Ketone 5 was found to be a competitive inhibitor of the dehydrogenase from Streptococcus pyogenes with a K-I value of 6.7 mu M. We have also prepared the secondary alcohols UDP-6S-6C-methylglucose, 4a, and UDP-6R-6C-methylglucose, 4b. Compound 4a, but not 4b, was found to be a slow substrate for the dehydrogenase and was converted into the ketone inhibitor 5. This is consistent with the notion that the pro-R hydride is transferred in the first oxidation step of the normal enzymatic reaction.

  DOI：

  10.1021/jo991092h
• 作为产物：
  描述：

  7-deoxy-1,2:3,5-di-O-isopropylidene-L-glycero-α-D-gluco-heptofuranose 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 6,7-dideoxy-1,2:3,5-di-O-isopropylidene-6-C-methyl-α-D-gluco-hept-6-enofuranose
  参考文献：
  名称：

  UDP-Glucose Analogues as Inhibitors and Mechanistic Probes of UDP-Glucose Dehydrogenase

  摘要：

  UDP-glucose dehydrogenase catalyzes the NAD(+)-dependent 2-fold oxidation of UDP-glucose to give UDP-glucuronic acid. The putative aldehyde intermediate is not released from the active site and is presumably tightly bound. We have prepared UDP-7-deoxy-alpha-D-gluco-hept-6-ulopyranose 5, that contains a methyl ketone at C-6 and cannot be further oxidized by the enzyme. Ketone 5 was found to be a competitive inhibitor of the dehydrogenase from Streptococcus pyogenes with a K-I value of 6.7 mu M. We have also prepared the secondary alcohols UDP-6S-6C-methylglucose, 4a, and UDP-6R-6C-methylglucose, 4b. Compound 4a, but not 4b, was found to be a slow substrate for the dehydrogenase and was converted into the ketone inhibitor 5. This is consistent with the notion that the pro-R hydride is transferred in the first oxidation step of the normal enzymatic reaction.

  DOI：

  10.1021/jo991092h

文献信息

• UDP-Glucose Analogues as Inhibitors and Mechanistic Probes of UDP-Glucose Dehydrogenase
  作者：Robert E. Campbell、Martin E. Tanner

  DOI：10.1021/jo991092h

  日期：1999.12.1

  UDP-glucose dehydrogenase catalyzes the NAD(+)-dependent 2-fold oxidation of UDP-glucose to give UDP-glucuronic acid. The putative aldehyde intermediate is not released from the active site and is presumably tightly bound. We have prepared UDP-7-deoxy-alpha-D-gluco-hept-6-ulopyranose 5, that contains a methyl ketone at C-6 and cannot be further oxidized by the enzyme. Ketone 5 was found to be a competitive inhibitor of the dehydrogenase from Streptococcus pyogenes with a K-I value of 6.7 mu M. We have also prepared the secondary alcohols UDP-6S-6C-methylglucose, 4a, and UDP-6R-6C-methylglucose, 4b. Compound 4a, but not 4b, was found to be a slow substrate for the dehydrogenase and was converted into the ketone inhibitor 5. This is consistent with the notion that the pro-R hydride is transferred in the first oxidation step of the normal enzymatic reaction.