1,2,3,5,6-penta-O-acetyl-D-galactofuranose

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,5,6-penta-O-acetyl-D-galactofuranose
• 英文别名: penta-O-acetyl-D-galactofuranose；per-O-acetyl D-galactofuranose；D-Galactofuranose Pentaacetate；[(2R)-2-acetyloxy-2-[(2S,3S,4R)-3,4,5-triacetyloxyoxolan-2-yl]ethyl] acetate
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: JRZQXPYZEBBLPJ-RRMRAIHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,3,5,6-penta-O-acetyl-D-galactofuranose 在 三氟化硼乙醚 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 6-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of galactofuranose-containing disaccharides using thioimidoyl-type donors

  摘要：

  Four galactofuranose-containing disaccharides have been prepared utilising various thioimidates [Galf-SC(=NR)XR'] and suitably protected acceptors as key precursors. We observed that the efficiency of the coupling reactions was particularly dependent on the aglycon present on the furanosyl donor when copper(II) ions were used as the promoter, and that activation could be correlated with the nature of the third heteroatorn, X. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.001
• 作为产物：
  描述：

  n-octyl D-galactofuranoside 在 吡啶 、 硫酸 、 溶剂黄146 作用下， 生成 1,2,3,5,6-penta-O-acetyl-D-galactofuranose
  参考文献：
  名称：

  An original chemoenzymatic route for the synthesis of β-d-galactofuranosides using an α-l-arabinofuranosidase

  摘要：

  Galactofuranose is a widespread component of cell wall polysaccharides in bacteria, protozoa and fungi, but is totally absent in mammals. Importantly, galactofuranose is a key constituent of major cell envelope polysaccharides in pathogenic mycobacteria. In this respect, galactofaranose-based glycoconjugates are interesting target molecules for drug design. O-Glycosidases and notably beta-D-galactofuranosidases could be useful tools for the chemoenzymatic synthesis of galacto furano sides, but to date no studies of this type have been reported. Here we report the use of a GH 51 alpha-L-arabinofuranosidase for the synthesis Of beta-D-galactofuranosides. We have demonstrated that this enzyme can catalyse both the autocondensation of p-nitrophenyl-beta-D-galactofuranoside and the transgalactofuranosylation of benzyl alpha-D-xylopyranoside, forming p-nitrophenyl beta-D-galactofuranosyl-(1 -> 2)beta-D-galactofuranoside and benzyl beta-D-galactofuranosyl-(1 -> 2)-alpha-D-xylopyranoside, respectively. Both reactions were very regiospecific and the reaction involving benzyl alpha-D-xylopyranoside afforded very high yields (74.8%) of the major product. To our knowledge, this demonstration of chemoenzymatic synthesis of galactofuranosides constitutes the very first use of an O-glycosidase for the synthesis of galactofuranosides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.01.016

文献信息

• [EN] REMOVAL OF SENESCENCE-ASSOCIATED MACROPHAGES<br/>[FR] ÉLIMINATION DE MACROPHAGES ASSOCIÉS À LA SÉNESCENCE
  申请人：EVERON BIOSCIENCES INC

  公开号：WO2017189553A1

  公开（公告）日：2017-11-02

  In various aspects and embodiments provided are compounds, compositions and methods relating to aging, senescent cells (SCs) and/or senescence associate macrophages (SAMs). In certain aspects and embodiments provided are compounds and compositions that selectively kill or reprogram senescent cells (SCs) and or senescence associate macrophages (SAMs) and associated methods. In some embodiments, the compounds compositions and methods treat or reverse aging and/or age-related diseases.

  在提供的各种方面和实施例中，涉及与衰老、衰老细胞（SCs）和/或衰老相关巨噬细胞（SAMs）有关的化合物、组合物和方法。在某些方面和实施例中，提供了选择性杀死或重新编程衰老细胞（SCs）和/或衰老相关巨噬细胞（SAMs）的化合物和组合物以及相关方法。在一些实施例中，这些化合物、组合物和方法用于治疗或逆转衰老和/或与年龄相关的疾病。
• General One-Step Synthesis of Free Hexofuranosyl 1-Phosphates Using Unprotected 1-Thioimidoyl Hexofuranosides
  作者：Ronan Euzen、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1021/jo0484934

  日期：2005.2.1

  synthesis of hexofuranosyl 1-phosphates starting from new unprotected glycofuranosyl donors. It required first the preparation of new 1-thiohexofuranosides bearing a thioimidoyl heterocycle as a leaving group. The presence of sulfur and/or nitrogen atom(s) on the aglycon allowed remote activation of these thioglycofuranosides by anhydrous phosphoric acid and led to the target phosphates 9, 27, 29, and 30

  从新的未保护的糖呋喃糖基供体开始，开发了用于合成呋喃糖基1-磷酸酯的一般的一步策略。它首先需要制备带有硫代酰亚胺基杂环作为离去基团的新的1-硫己呋喃呋喃糖苷。硫和/或氮原子（一个或多个）上的糖苷配基的存在使得这些thioglycofuranosides的远程激活通过无水磷酸，并导致目标磷酸盐9，27，29，和30具有良好的选择性至极好的选择性，更重要的是，环扩展非常有限或没有。此外，通过避免对带负电荷的化合物进行任何繁琐的保护基操作并着重于简单但通用的纯化程序，可以显着改善这一一步的磷酸化反应。该方法被用于d-半乳糖和d-呋喃呋喃糖基1-磷酸的非对映控制合成，还用于制备稀有的差向异构体和/或脱氧对应物，即d-甘露糖醛和d-呋喃呋喃糖基衍生物。
• Two-Step Synthesis of Per-<i>O</i>-acetylfuranoses: Optimization and Rationalization
  作者：Rémy Dureau、Laurent Legentil、Richard Daniellou、Vincent Ferrières

  DOI：10.1021/jo201913f

  日期：2012.2.3

  A simple two-step procedure yielding peracetylated furanoses directly from free aldoses was implemented. Key steps of the method are (i) highly selective formation of per-O-(tert-butyldimethylsilyl)furanoses and (ii) their clean conversion into acetyl ones without isomerization. This approach was easily applied to galactose and structurally related carbohydrates such as arabinose, fucose, methyl galacturonate

  实现了一个简单的两步程序，直接从游离醛糖中产生过乙酰化呋喃糖酶。该方法的关键步骤是（i）高选择性形成过-O-（叔丁基二甲基甲硅烷基）呋喃糖和（ii）在不异构化的情况下将其干净地转化为乙酰基。这种方法很容易应用于半乳糖和与结构相关的碳水化合物，例如阿拉伯糖，岩藻糖，半乳糖醛酸甲酯和N-乙酰半乳糖胺得到相应的过乙酰化目标。该方法的成功取决于至少三个参数的控制：（i）起始未保护糖的互变异构平衡，（ii）靶向呋喃糖酶和甲硅烷基化剂的空间位阻，最后，（iii）保护基相互转化期间的每个软亲核试剂。
• Identification and Characterization of a Novel Galactofuranose-Specific β-D-Galactofuranosidase from Streptomyces Species
  作者：Emiko Matsunaga、Yujiro Higuchi、Kazuki Mori、Nao Yairo、Takuji Oka、Saki Shinozuka、Kosuke Tashiro、Minoru Izumi、Satoru Kuhara、Kaoru Takegawa

  DOI：10.1371/journal.pone.0137230

  日期：——

  β-D-galactofuranose (Galf) is a component of polysaccharides and glycoconjugates and its transferase has been well analyzed. However, no β-D-galactofuranosidase (Galf-ase) gene has been identified in any organism. To search for a Galf-ase gene we screened soil samples and discovered a strain, identified as a Streptomyces species by the 16S ribosomal RNA gene analysis, that exhibits Galf-ase activity for 4-nitrophenyl β-D-galactofuranoside (pNP-β-D-Galf) in culture supernatants. By draft genome sequencing of the strain, named JHA19, we found four candidate genes encoding Galf-ases. Using recombinant proteins expressed in Escherichia coli, we found that three out of four candidates displayed the activity of not only Galf-ase but also α-L-arabinofuranosidase (Araf-ase), whereas the other one showed only the Galf-ase activity. This novel Galf-specific hydrolase is encoded by ORF1110 and has an optimum pH of 5.5 and a Km of 4.4 mM for the substrate pNP-β-D-Galf. In addition, this enzyme was able to release galactose residue from galactomannan prepared from the filamentous fungus Aspergillus fumigatus, suggesting that natural polysaccharides could be also substrates. By the BLAST search using the amino acid sequence of ORF1110 Galf-ase, we found that there are homolog genes in both prokaryotes and eukaryotes, indicating that Galf-specific Galf-ases widely exist in microorganisms.

  β-D-半乳糖呋喃糖（Galf）是多糖和糖共轭物的一种成分，其转移酶已被充分分析。然而，目前尚未在任何生物体中发现β-D-半乳糖呋喃糖苷酶（Galf-ase）基因。为了寻找半乳呋喃糖苷酶基因，我们对土壤样本进行了筛选，发现了一株通过 16S 核糖体 RNA 基因分析确定为链霉菌的菌株，该菌株在培养上清液中对 4-硝基苯基 β-D-半乳呋喃糖苷（pNP-β-D-Galf）具有半乳呋喃糖苷酶活性。通过对这株名为 JHA19 的菌株进行基因组测序，我们发现了四个编码 Galf 酶的候选基因。通过在大肠杆菌中表达重组蛋白，我们发现四个候选基因中有三个不仅具有 Galf-酶的活性，而且还具有 α-L-阿拉伯呋喃糖苷酶（Araf-ase）的活性，而另一个则只具有 Galf-酶的活性。这种新型的 Galf 特异性水解酶由 ORF1110 编码，对底物 pNP-β-D-Galf 的最适 pH 值为 5.5，Km 为 4.4 mM。此外，这种酶还能从丝状真菌曲霉制备的半乳甘露聚糖中释放半乳糖残基，这表明天然多糖也可以是底物。通过对ORF1110半乳糖酶的氨基酸序列进行BLAST检索，我们发现原核生物和真核生物中都存在同源基因，这表明微生物中广泛存在半乳糖特异性半乳糖酶。
• 1,2-O-cyanoalkylidene derivatives of furanoses as 1,2-trans-glycosylating agents
  作者：Leon V. Backinowsky、Sergei A. Nepogod'ev、Alexander S. Shashkov、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(85)85221-6

  日期：1985.4

  with trimethylsilyl cyanide in acetonitrile in the presence of stannous chloride gave the respective 1,2-O-(1-cyanoethylidene) derivatives. Triphenyl-methylium perchlorate-catalysed glycosylation of trityl ethers of monosaccharides by the above cyanoethylidene derivatives and by 3,5-di-O-benzoyl-1,2-O-(α-cyanobenzylidene)-β-l-arabinofuranose gave high yields of protected disaccharides containing a

  在氯化亚锡存在下，在乙腈中用三甲基甲硅烷基氰化物处理乙酰化的1-阿拉伯呋喃糖，d-半乳糖呋喃糖和d-葡萄糖呋喃糖，分别得到1,2-O-（1-氰基亚乙基）衍生物。上述氰基亚乙基衍生物和3,5-二-O-苯甲酰基-1,2-O-（α-氰基苄叉基）-β-1-阿拉伯呋喃糖的三苯基甲基高氯酸盐催化的单糖三苯甲基醚的糖基化反应产生了高收率的被保护的含有1，2-反式-呋喃糖苷键的二糖。