D-mannose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-mannose
• 英文别名: (4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
• 化学式: C₆H₁₂O₆
• 分子量: 180.158
• InChiKey: WQZGKKKJIJFFOK-MNQXGKBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  12
• 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：

  D-mannose 在 硫酸 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 17.0h， 生成 D-glycero-D-talo-heptonic acid 4-lactone
  参考文献：
  名称：

  Acetonides of heptonolactones: Powerful chirons

  摘要：

  Heptonolactones, in which all the functional groups except one can be protected with a single ketal protecting group, have great potential as starting materials within the chiral pool. The practical synthesis and characterisation of acetonides of glycero-talo- and glycero-galacto-heptono-lactone are described. X-ray crystal structures of D-glycero-D-talo-heptono-1,4-lactone and 2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone are reported.

  DOI：

  10.1016/s0957-4166(00)82201-6
• 作为产物：
  描述：

  sonneradon D 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 D-mannose
  参考文献：
  名称：

  Compounds from the fruits of mangrove Sonneratia apetala: Isolation, molecular docking and antiaging effects using a Caenorhabditis elegans model

  摘要：

  The chemical investigation of the fruits of a mangrove Sonneratia apetala collected from the Beibu Gulf led to the isolation of four new compounds, sonneradons A-D (1-4), as well as 18 known compounds (5-22). The structures of the new compounds were elucidated based on extensive spectroscopic analysis, and the structures of the known compounds were established by comparison of their spectroscopic data with those of related metabolites. The antiaging activities of all isolates were evaluated using the nematode Caenorhabditis elegans as a model organism. The results showed that 10 compounds could protect C. elegans by extending its lifespan. Compound 1 possessed the most potent effect in the anti-heat stress assay and significantly attenuated aging-related decreases in the pumping and bending of the nematodes in the healthspan assay. Molecular docking studies suggested that compound 1 was bound to the DNA binding domain of HSF-1 and promoted the conformation of HSF-1, thus strengthening the interaction between the HSF-1 and related DNA. GLN49, ASN-74, and LYS-80 of the binding region might be the key amino residues during the interaction.

  DOI：

  10.1016/j.bioorg.2020.103813

文献信息

• US7883687B2
  申请人：——

  公开号：US7883687B2

  公开（公告）日：2011-02-08
• Acetonides of heptonolactones: Powerful chirons
  作者：Annabel R. Beacham、Ian Bruce、Samuel Choi、Orla Doherty、Antony J. Fairbanks、George W.J. Fleet、Ben M. Skead、Josephine M. Peach、John Saunders、David J. Walking

  DOI：10.1016/s0957-4166(00)82201-6

  日期：1991.1

  Heptonolactones, in which all the functional groups except one can be protected with a single ketal protecting group, have great potential as starting materials within the chiral pool. The practical synthesis and characterisation of acetonides of glycero-talo- and glycero-galacto-heptono-lactone are described. X-ray crystal structures of D-glycero-D-talo-heptono-1,4-lactone and 2,3:5,6-di-O-isopropylidene-D-glycero-D-talo-heptono-1,4-lactone are reported.
• Compounds from the fruits of mangrove Sonneratia apetala: Isolation, molecular docking and antiaging effects using a Caenorhabditis elegans model
  作者：Xiangxi Yi、Shu Jiang、Mei Qin、Kai Liu、Pei Cao、Shimin Chen、Jiagang Deng、Chenghai Gao

  DOI：10.1016/j.bioorg.2020.103813

  日期：2020.6

  The chemical investigation of the fruits of a mangrove Sonneratia apetala collected from the Beibu Gulf led to the isolation of four new compounds, sonneradons A-D (1-4), as well as 18 known compounds (5-22). The structures of the new compounds were elucidated based on extensive spectroscopic analysis, and the structures of the known compounds were established by comparison of their spectroscopic data with those of related metabolites. The antiaging activities of all isolates were evaluated using the nematode Caenorhabditis elegans as a model organism. The results showed that 10 compounds could protect C. elegans by extending its lifespan. Compound 1 possessed the most potent effect in the anti-heat stress assay and significantly attenuated aging-related decreases in the pumping and bending of the nematodes in the healthspan assay. Molecular docking studies suggested that compound 1 was bound to the DNA binding domain of HSF-1 and promoted the conformation of HSF-1, thus strengthening the interaction between the HSF-1 and related DNA. GLN49, ASN-74, and LYS-80 of the binding region might be the key amino residues during the interaction.