benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside | 914642-50-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside
• 英文别名: 2-(benzenesulfonyl)ethyl (2R)-2-[(2S,3R,4R,5S,6R)-3-acetamido-5-hydroxy-2-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxypropanoate
• CAS: 914642-50-5
• 化学式: C₃₃H₃₉NO₁₀S
• 分子量: 641.739
• InChiKey: QQSBMIGWGWKLFJ-VMDTVNBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 铜 、 zinc(II) chloride 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 57.0h， 生成 2-(benzenesulfonyl)ethyl (2R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-3-[(2S,3R,4S,6S)-3-acetamido-4-acetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-(acetyloxymethyl)-6-phenylmethoxyoxan-4-yl]oxypropanoate
  参考文献：
  名称：

  用于修饰脂质 II 合成的脱氧双糖前体的合成

  摘要：

  描述了用于修饰脂质 II 合成的新型脱氧二糖前体的合成。通过 TBTH/AIBN 自由基还原碘衍生物和使用硼氢化物试剂 (nBu4NBH4) 氢还原三氟甲磺酸酯，分别获得 3-和 4-脱氧-GlcNAc 供体。NIS/TMSOTf 促进受体的 O-糖基化，产生 3-和 4-脱氧二糖。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600515
• 作为产物：
  描述：

  D-GlcNAc 在 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟甲磺酸 、 sodium hydride 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 乙酰氯 、 原甲酸三乙酯 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Peptidoglycan Units with UDP at the Anomeric Position

  摘要：

  一系列UDP-二糖肽化合物被合成为糖基转移酶的合成底物类似物或潜在抑制剂。已经制备了荧光化合物，目的是开发一种筛选方法，用于选择转糖基酶抑制剂。

  DOI：

  10.1135/cccc20051615

文献信息

• Synthesis of Modified Peptidoglycan Precursor Analogues for the Inhibition of Glycosyltransferase
  作者：Shrinivas Dumbre、Adeline Derouaux、Eveline Lescrinier、André Piette、Bernard Joris、Mohammed Terrak、Piet Herdewijn

  DOI：10.1021/ja302099u

  日期：2012.6.6

  The peptidoglycan glycosyltransferases (GTs) are essential enzymes that catalyze the polymerization of On OH glycan chains of the bacterial cell wall from lipid II and thus constitute a validated antibacterial target. Their enzymatic cavity is composed of a donor site for the growing glycan chain (where the inhibitor moenomycin binds) and an acceptor site for lipid II substrate. In order to find lead inhibitors able to fill this large active site, we have synthesized a series of substrate analogues of lipid I and lipid II with variations in the lipid, the pyrophosphate, and the peptide moieties and evaluated their biological effect on the GT activity of E. coli PBP1b and their antibacterial potential. We found several compounds able to inhibit the GT activity in vitro and cause growth defect in Bacillus subtilis. The more active was C16-phosphoglycerate-MurNAc-(L-Alao-D-Glu)-GIcNAc, which also showed antibacterial activity. These molecules are promising leads for the design of new antibacterial GT inhibitors.
• Characterization of a transglycosylase domain of Streptococcus pneumoniae PBP1b
  作者：Haitian Liu、Chi-Huey Wong

  DOI：10.1016/j.bmc.2006.06.058

  日期：2006.11

  Inhibitors of transglycosylases may serve as potent antibiotics that are less prone to resistance development in bacterial pathogens. To facilitate the search of such compounds, a transglycosylase (TGase) domain of the membrane integral multidomain Streptococcus pneumoniae PBP1b was cloned and expressed. This TGase domain was characterized by a substrate-dependent fluorescence coupled enzyme assay and an inhibitor-tethered surface plasmon resonance binding assay. Both assays show that the catalytic efficiency of the domain is comparable to that of the monofunctional transglycosylases, and it is fully active in the absence of other domains. The isolation of the active TGase domain makes it possible to screen for potential antibiotics targeting transglycosylases. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of Peptidoglycan Units with UDP at the Anomeric Position
  作者：Thierry Lioux、Roger Busson、Jef Rozenski、Martine Nguyen-Distèche、Jean-Marie Frère、Piet Herdewijn

  DOI：10.1135/cccc20051615

  日期：——

  A series of UDP-disaccharide peptide compounds were synthesized as synthetic substrate analogues or potential inhibitors of glycosyl transferase. Fluorescent compounds have been prepared with the aim of developing a screening method for selecting transglycosylase inhibitors.

  一系列UDP-二糖肽化合物被合成为糖基转移酶的合成底物类似物或潜在抑制剂。已经制备了荧光化合物，目的是开发一种筛选方法，用于选择转糖基酶抑制剂。
• Synthesis of Deoxygenated Disaccharide Precursors for Modified Lipid II Synthesis
  作者：De-Qun Sun、Roger Busson、Piet Herdewijn

  DOI：10.1002/ejoc.200600515

  日期：2006.11

  The synthesis of novel deoxygenated disaccharide precursors for modified lipid II synthesis is described. The 3- and 4-deoxy-GlcNAc donors were obtained, respectively, by radical reduction of the iodo derivative by TBTH/AIBN and hydrogen reduction of the triflate using a borohydride reagent (nBu4NBH4). O-Glycosylation of the acceptor, promoted by NIS/TMSOTf, led to the 3- and 4-deoxygenated disaccharides

  描述了用于修饰脂质 II 合成的新型脱氧二糖前体的合成。通过 TBTH/AIBN 自由基还原碘衍生物和使用硼氢化物试剂 (nBu4NBH4) 氢还原三氟甲磺酸酯，分别获得 3-和 4-脱氧-GlcNAc 供体。NIS/TMSOTf 促进受体的 O-糖基化，产生 3-和 4-脱氧二糖。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)