D-galactono-1,5-lactone | 15892-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-galactono-1,5-lactone
• 英文别名: D-galactonolactone；(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
• CAS: 15892-28-1
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: PHOQVHQSTUBQQK-MGCNEYSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-galactono-1,5-lactone 在 氧气 、 lithium hydroxide 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以40%的产率得到D-lyxose
  参考文献：
  名称：

  Degradation of Unprotected Aldohexonic Acids to Aldopentoses Promoted by Light and Oxygen

  摘要：

  Herein reported is a photoredox-catalyzed oxidative degradation reaction of unprotected aldohexonic acids, which are shortened by one-carbon to the corresponding aldopentoses. Oxygen including aerial oxygen is used as a terminal oxidant. The mild reaction conditions permit even disaccharides to successfully undergo the degradation reaction with the glycosidic bond remaining intact. Quinic acid is also converted to a useful chiral synthetic intermediate.

  DOI：

  10.1246/cl.200517
• 作为产物：
  描述：

  D-半乳糖酸-1,4-内酯 以 异丙醇 为溶剂， 生成 D-galactono-1,5-lactone
  参考文献：
  名称：

  A Simple Synthesis of D-Galactono-1,4-Lactone and Key Building Blocks for the Preparation of Galactofuranosides

  摘要：

  The oxidation of D-galactose by Br-2 to yield D-galactono-1,4-lactone was developed and applied to the preparation of key building blocks for the synthesis of galactofuranosides. Three D-galactono-1,4-lactone derivatives protected as acetates, TBDMS ether, or acetonide were directly obtained in two steps on multigram scale with only one purification step. A mild deacetylation methodology afforded pure D-galactono-1,4-lactone and a new reduction of the lactone functionality using K-selectride was also optimized.

  DOI：

  10.1080/07328303.2011.616273

文献信息

• Solubilization, Purification, and Properties of Membrane-Bound<scp>D</scp>-Glucono-δ-lactone Hydrolase from<i>Gluconobacter oxydans</i>
  作者：Emiko SHINAGAWA、Yoshitaka ANO、Toshiharu YAKUSHI、Osao ADACHI、Kazunobu MATSUSHITA

  DOI：10.1271/bbb.80554

  日期：2009.1.23

  Membrane-bound glucono-δ-lactonase (MGL) was purified to homogeneity from the membrane fraction of Gluconobacter oxydans IFO 3244. After solubilization with 1 m CaCl2, MGL was purified in the presence of Ca2+ and detergent. A single band corresponding to 60 kDa appeared in SDS–PAGE. The molecular weight of MGL was judged to be 120k. Differently from cytoplasmic lactonases, MGL showed optimum pH in an acidic range of 5–5.5. It was highly sensitive to metal-chelating agents such as EDTA, and the lost MGL activity was restored to the original level by the addition of divalent cations such as Ca2+ or Mg2+. The purified MGL was strictly dependent on Ca2+ and underwent rapid denaturing precipitation on Ca2+ depletion even in the presence of detergent. This communication can be the first one dealing with the solubilization, purification and properties of MGL.

  膜结合D-葡萄糖酸-δ-内酯酶（MGL）从Gluconobacter oxydans IFO 3244的膜部分纯化至均一性。在采用1 m CaCl2溶解后，MGL在Ca2+和洗涤剂的存在下得到纯化。SDS-PAGE中出现对应于60 kDa的单一条带。MGL的分子量判断为120k。与细胞质内酯酶不同，MGL在pH 5-5.5的酸性范围内显示出最适pH。它对金属螯合剂如EDTA高度敏感，失去的MGL活性可以通过添加如Ca2+或Mg2+等二价阳离子恢复至原始水平。纯化的MGL严格依赖于Ca2+，并且在即使有洗涤剂存在下，由于Ca2+的缺失而迅速发生变性沉淀。这份交流可能是首次涉及MGL的溶解、纯化和性质的研究。
• [EN] A GLUCOPYRANOSYL DERIVATIVE AND PREPARATION METHOD AND USES THEREOF<br/>[FR] DÉRIVÉ DE GLUCOPYRANOSYLE, SON PROCÉDÉ DE PRÉPARATION ET SES UTILISATIONS
  申请人：SUNSHINE LAKE PHARMA CO LTD

  公开号：WO2016173425A1

  公开（公告）日：2016-11-03

  This present invention relates to a glucopyranosyl derivative as sodium dependent glucose cotransporters (SGLTs) inhibitor, preparation processes thereof, and pharmaceutical uses thereof, pharmaceutical compositions containing the compound and their uses for treating diabetes and diabetes-related diseases. The process of the invention has simple operation, high optical purity of product, high yield and convenient work-up, easy purification, and is suitable for industrial production.

  本发明涉及一种葡萄糖吡喃糖苷衍生物，作为钠依赖型葡萄糖共转运蛋白（SGLTs）抑制剂，以及其制备方法、药用用途，包含该化合物的药用组合物及其用于治疗糖尿病和糖尿病相关疾病的用途。该发明的制备过程操作简单，产品光学纯度高，产率高，操作方便，易于纯化，并适用于工业生产。
• Stability of aminooxy glycosides to glycosidase catalysed hydrolysis
  作者：Amjid Iqbal、Hicham Chibli、Chris J. Hamilton

  DOI：10.1016/j.carres.2013.05.006

  日期：2013.8

  amino(methoxy) beta-glycosidic bond to glycosidase catalysed hydrolysis is reported. Beta-O-benzyl glucose and beta-O-benzyl galactose are substrates hydrolysed by beta-glucosidase and beta-galactosidase from almonds and Escherichia coli, respectively. However their beta-N-benzyl-(O-methoxy)-glucoside and beta-N-benzyl-(O-methoxy)-galactoside derivatives are competitive inhibitors.

  报道了氨基（甲氧基）β-糖苷键对糖苷酶催化水解的稳定性。β-O-苄基葡萄糖和β-O-苄基半乳糖分别是分别来自杏仁和大肠杆菌的β-葡萄糖苷酶和β-半乳糖苷酶水解的底物。然而，它们的β-N-苄基-（O-甲氧基）-葡糖苷和β-N-苄基-（O-甲氧基）-半乳糖苷衍生物是竞争性抑制剂。
• Convergent synthesis of D-(−)-quinic and shikimic acid-containing dendrimers as potential C-lectin ligands by sulfide ligation of unprotected fragments
  作者：Cyrille Grandjean、Corinne Rommens、Hélène Gras-Masse、Oleg Melnyk

  DOI：10.1039/a904679h

  日期：——

  The preparation of D-(–)-quinic and (–)-shikimic acid-derived dendrimers with valencies of 4, 8 and 16, respectively, as potential C-lectin ligands is reported. D-(–)-Quinic and shikimic acids were branched to an (S-tert-butylthio-L-cysteine)-containing tripeptide on solid phase to furnish compounds 1 and 3. These intermediates were reduced upon treatment with tri-n-butylphosphine and linked to N-chloroacetylated L-lysinyl cores via a nucleophilic substitution performed in aqueous DMF.

  本文报道了以 D-(–)-奎宁酸和 (–)-香草酸为基础的树形分子，其配位数分别为 4、8 和 16，作为潜在的 C-凝集素配体。D-(–)-奎宁酸和香草酸在固相上与含有 (S-tert-丁硫-L-半胱氨酸) 的三肽交联，生成化合物 1 和 3。这些中间体在与三正丁基膦反应后被还原，并通过在水相 DMF 中进行的亲核取代反应与 N-氯乙酰化的 L-赖氨酸骨架连接。
• Synthesis and interfacial properties of new 6-sulfate sugar-based anionic surfactants
  作者：Bemba Abdellahi、Rémy Bois、Sema Golonu、Gwladys Pourceau、David Lesur、Vincent Chagnault、Audrey Drelich、Isabelle Pezron、Alla Nesterenko、Anne Wadouachi

  DOI：10.1016/j.tetlet.2021.153113

  日期：2021.6

  chain. Twelve of the as-synthesized anionic glycolipids, including nine novel sulfated compounds, were investigated for their surface activity at the air/liquid interface and for their self-assembling properties. These sugar-based surfactants show surface properties similar to those of commercial anionic surfactants (SDS and SLES) with good ability to reduce surface tension. The obtained results confirm

  合成了三族在单糖的主要位置上带有硫酸盐官能团的阴离子糖基表面活性剂，并比较了它们的理化性质。第一家庭对应于市售的八- 6-硫酸衍生物和十二烷基β- d -葡糖- 和吡喃半乳糖苷。第二个和第三个家族在硫酸化单糖（半乳糖、葡萄糖或木糖）和疏水性烷基链之间包含一个酰胺接头。研究了 12 种合成的阴离子糖脂（包括 9 种新型硫酸化化合物）在空气/液体界面的表面活性和自组装性能。这些糖基表面活性剂的表面特性与商业阴离子表面活性剂（SDS 和 SLES）相似，具有良好的降低表面张力的能力。获得的结果证实了人们对这些新的生物基分子在各种配方中潜在替代阴离子表面活性剂的兴趣。