7-deoxy-L-glycero-D-gluco-heptopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-deoxy-L-glycero-D-gluco-heptopyranose
• 英文别名: (3R,4S,5S,6R)-6-[(1S)-1-hydroxyethyl]oxane-2,3,4,5-tetrol
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: PZODEECXPHBZCU-JMAICNALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sodium acetate 、 7-deoxy-L-glycero-D-gluco-heptopyranose 在 乙酸酐 作用下， 以48%的产率得到1,2,3,4,6-pentacetyl-7-deoxy-L-glycero-β-D-gluco-heptopyranose
  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：

  D-glucurono-3,6-lactone acetonide 在 咪唑 、 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-deoxy-L-glycero-D-gluco-heptopyranose
  参考文献：
  名称：

  D-葡萄糖和L-岩藻糖的7-碳模拟物：糖原合酶的6R-激活和6S，-6C-甲基葡萄糖的失活：葡萄糖激酶和/或葡萄糖-6-磷酸酶的抑制

  摘要：

  描述了差向异构的C 6 -C-甲基葡萄糖的短效合成。一个C-6差向异构体激活糖原合酶，而另一个差向异构体失活该酶。C 6 R -C-甲基葡萄糖3是葡萄糖6磷酸酶的特异性抑制剂的第一个实例，并且可以使细胞内葡萄糖6磷酸的浓度增加20倍。C 6 S -C-甲基葡萄糖2抑制葡萄糖激酶和葡萄糖6-磷酸酶，但也具有容易获得L-岩藻糖的α - C-糖苷的潜力。C-6-烷基碳水化合物可提供一系列新的糖模拟物，以控制与糖-6-磷酸的形成，水解和其他命运相关的酶。

  DOI：

  10.1016/0040-4039(96)01565-1

文献信息

• EP0593419A4
  申请人：——

  公开号：EP0593419A4

  公开（公告）日：1994-08-17
• INHIBITORS FOR GLYCOSAMINOSYL TRANSFERASE-V
  申请人：CHEMBIOMED, LTD.

  公开号：EP0593419A1

  公开（公告）日：1994-04-27
• US5032505A
  申请人：——

  公开号：US5032505A

  公开（公告）日：1991-07-16
• [EN] INHIBITORS FOR GLYCOSAMINOSYL TRANSFERASE-V
  申请人：——

  公开号：WO1990005527A1

  公开（公告）日：1990-05-31

  [FR] Des accepteurs et des inhibiteurs synthétiques de glycosaminosyl transférase-V sont décrits. Les inhibiteurs et accepteurs minimum de trisaccharide spécifiques pour le GnT-V, associé à la capacité de cellules de se transformer par métabolisme, sont utiles dans le diagnostic et le traitement d'états caractérisés par des cellules métastatiques.
  [EN] Synthetic glycosaminosyl transferase-V acceptors and inhibitors are disclosed. Minimal trisaccharide inhibitors and acceptors specific for GnT-V, which is associated with the ability of cells to metastasize are useful, in diagnosis and treatment of conditions characterized by metastatic cells.
• 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.