methyl 5-O-p-toluenesulfonyl-α-D-arabinofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-O-p-toluenesulfonyl-α-D-arabinofuranoside
• 英文别名: [(2R,3S,4S,5S)-3,4-dihydroxy-5-methoxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• 化学式: C₁₃H₁₈O₇S
• 分子量: 318.348
• InChiKey: XBVIMOJKPKLGTL-NDBYEHHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 5-O-p-toluenesulfonyl-α-D-arabinofuranoside 在 吡啶 、 sodium azide 、 三氟化硼乙醚 、 氨 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.0h， 生成 octyl 5-S-(5-deoxy-5-azido-β-D-arabinofuranosyl)-5-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  硫连接的阿拉伯呋喃糖基二糖的设计、合成和活性对结核分枝杆菌 (MTB) 和鸟分枝杆菌复合体 (MAC)

  摘要：

  我们报告了一系列带有糖苷硫接头的阿拉伯呋喃糖二糖的化学合成，作为阿拉伯呋喃基转移酶受体的模拟物，使用或不使用任何激活剂以避免任何复杂反应。测试了这些类似物对 MTB 菌株 H37Ra 和 3 个 MAC 临床分离株的体外活性。MIC 使用比色微量稀释肉汤测定来确定。杀菌活性是用 7 天的杀菌曲线研究的。在 Mono Mac 6 (MM6) 人单核细胞系中测定了针对 MTB H37Ra 的细胞内活性。

  DOI：

  10.3998/ark.5550190.0014.222
• 作为产物：
  描述：

  阿拉伯糖 在 吡啶 作用下， 反应 24.0h， 生成 methyl 5-O-p-toluenesulfonyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Preparation of Amino Alcohols Condensed with Carbohydrates: Evaluation of Cytotoxicity and Inhibitory Effect on NO Production

  摘要：

  This work reports the preparation of several amino alcohols condensed with d‐arabinose, d‐glucose, and d‐galactose derivatives. These compounds were evaluated in vitro for their cytotoxicity and ability to decrease nitric oxide production in J774A.1 cells. Arabinofuranoside derivatives 5a, 5b and 5c showed a significant inhibition of nitric oxide production (>80% at 5 μg/mL), while the galactopyranoside derivative 8d showed a notable nitric oxide inhibitory activity (126% at 0.5 μg/mL).

  DOI：

  10.1111/j.1747-0285.2010.01026.x

文献信息

• Analogues of Moranoline and Mdl 73945. Methyl 6(5)-Deoxy-6(5)-(Morpholin-4-Yl)-α-D-Glycosides as Glucosidase Inhibitors
  作者：El Sayed H. El Ashry、Adel A.-H. Abdel-Rahman、Mohamed Kattab、Aida H. Shobier、Richard R. Schmidt

  DOI：10.1080/07328300008544083

  日期：2000.1

  Methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside (6), or its iodo analogue 7, were subjected to nucleophilic displacement with morpholine to give 8, deacetylation of which gave methyl 6-deoxy-6-(morpholin-4-yl)-α-D-glucopyranoside (3). Similarly, 11, 12 and 21 were prepared. The 6-deoxy-6-iodo derivative 16 was subjected to nucleophilic displacement with morpholine and subsequent

  摘要将甲基2,3,4-三-O-乙酰基-6-O-（对甲苯磺酰基）-α-D-吡喃葡萄糖苷（6）或其碘代类似物7进行吗啉的亲核置换，得到8，脱乙酰基得到甲基6-脱氧-6-（吗啉-4-基）-α-D-吡喃葡萄糖苷（3）。类似地，准备了11、12和21。用吗啉对6-脱氧-6-碘衍生物16进行亲核置换，然后乙酰化，得到15。15的脱乙酰基得到17。对甜杏仁中β-D-葡糖苷酶的抑制作用以及使用邻硝基苯的动力学研究以β-D-吡喃葡萄糖苷为底物的K i值与1-脱氧野n霉素的顺序相同，而对于3，观察到的K i值较小。
• Design, Synthesis, and X-ray Analysis of a Glycoconjugate Bound to Mycobacterium tuberculosis Antigen 85C
  作者：Diaa A. Ibrahim、Julie Boucau、Daniel H. Lajiness、Sri Kumar Veleti、Kevin R. Trabbic、Samuel S. Adams、Donald R. Ronning、Steven J. Sucheck

  DOI：10.1021/bc3004342

  日期：2012.12.19

  Tuberculosis (TB) is a global health threat with nearly 500 000 new cases of multidrug-resistant TB estimated to occur every year, so new drugs are desperately needed. A number of current antimycobacterial drugs work by interfering with the biosynthesis of key components of the mycolylar-abinogalactan (mAG). In light of this observation, other enzymes involved in the synthesis of the mAG should also serve as targets for antimycobacterial drug development. One potential target is the Antigen 85 (Ag85) complex, a family of mycolyltransferases that are responsible for the transfer of mycolic acids from trehalose monomycolate (TMM) to the arabinogalactan. Virtual thiophenyl arabinoside conjugates were docked to antigen Ag85C (PDB code: 1va5) using Glide. Compounds with good docking scores were synthesized by a Gewald synthesis followed by linking to 5-thioarabinofuranosides. The resulting thiophenyl-thioarabinofuranosides were assayed for inhibition of mycoyltransferase activity using a 4-methylumbelliferyl butyrate fluorescence assay. The conjugates showed K-i values ranging from 18.2 to 71.0 mu M. The most potent inhibitor was soaked into crystals of Mycobacterium tuberculosis antigen 85C and the structure of the complex determined. The X-ray structure shows the compound bound within the active site of the enzyme with the thiophene moiety positioned in the putative alpha-chain binding site of TMM and the arabinofuranoside moiety within the known carbohydrate-binding site as exhibited for the Ag85B-trehalose crystal structure. Unexpectedly, no specific hydrogen bonding interactions are being formed between the arabinofuranoside and the carbohydrate-binding site of the active site suggesting that the binding of the arabinoside within this structure is driven by shape complementarily between the arabinosyl moiety and the carbohydrate binding site.
• Synthesis of methyl 5-S-alkyl-5-thio-d-arabinofuranosides and evaluation of their antimycobacterial activity
  作者：Aditya K. Sanki、Julie Boucau、Parijat Srivastava、Samuel S. Adams、Donald R. Ronning、Steven J. Sucheck

  DOI：10.1016/j.bmc.2008.03.062

  日期：2008.5

  The emergence of drug resistant tuberculosis necessitates a search for new antimycobacterial compounds. The antigen 85 (ag85) complex is a family of mycolyl transferases involved in the synthesis of trehalose-6,6'-dimycolate and the mycolated hexasaccharide motif found at the terminus of the arabinogalactan in mycobacterium. Enzymes involved in the synthesis of cell wall structures like these are potential targets for the development of new antiinfectives. To potentially inhibit the ag85 complex, methyl 5-S-alkyl-5-thio-arabinofuranoside analogues were designed based on docking studies with ag85C derived from Mycobacterium tuberculosis. The target arabinofuranosides were then synthesized and the antibacterial activity evaluated against Mycobacterium smegmatis ATCC 14468. Two of the compounds, 5-S-octyl-5-thio-alpha-D-arabinofuranoside (8) and 5-S-octyl-5-thio-beta-D-arabinofuranoside (11), showed MICs of 256 and 512 mu g/mL, respectively. Attempts to directly evaluate acyltransferase inhibitory activity of the arabinofuranosides against ag85C are also described. In conclusion, a new class of antimycobacterial arabinofuranosides has been discovered. Published by Elsevier Ltd.