methyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside | 162284-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5S,6R)-3-acetamido-5-hydroxy-2-methoxy-6-(phenylmethoxymethyl)oxan-4-yl] acetate
• CAS: 162284-51-7
• 化学式: C₁₈H₂₅NO₇
• 分子量: 367.399
• InChiKey: GODYPHGXNWTVSI-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside 在 吡啶 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 4 Angstroem molecular seives 、 sodium methylate 、 sodium hydride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-3-O-((R)-1'-carboxyethyl)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic Peptidoglycan Substrates for Penicillin-Binding Protein 5 of Gram-Negative Bacteria

  摘要：

  The major constituent of the bacterial cell wall, peptidoglycan, is comprised of repeating units of N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM) with an appended peptide. Penicillin-binding proteins (PBPs) are involved in the final stages of bacterial cell wall assembly. Two activities for PBPs are the cross-linking of the cell wall, carried out by DD-transpeptidases, and the DD-peptidase activity, that removes the terminal D-Ala residue from peptidoglycan. The DD-peptidase activity moderates the extent of the cell wall cross-linking. There exists a balance between the two activities that is critical for the well-being of bacterial cells. We have cloned and purified PBP5 of Escherichia coli. The membrane anchor of this protein was removed, and the enzyme was obtained as a soluble protein. Two fragments of the polymeric cell wall of Gram-negative bacteria (compounds 5 and 6) were synthesized. These molecules served as substrates for PBP5. The products of the reactions of PBP5 and compounds 5 and 6 were isolated and were shown to be D-Ala and the fragments of the substrates minus the terminal D-Ala. The kinetic parameters for these enzymic reactions were evaluated. PBP5 would appear to have the potential for turnover of as many as 1.4 million peptidoglycan strands within a single doubling time (i.e., generation) of E. coli.

  DOI：

  10.1021/jo035397e
• 作为产物：
  描述：

  甲基 2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷 在 吡啶 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.5h， 生成 methyl 2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthetic Peptidoglycan Substrates for Penicillin-Binding Protein 5 of Gram-Negative Bacteria

  摘要：

  The major constituent of the bacterial cell wall, peptidoglycan, is comprised of repeating units of N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM) with an appended peptide. Penicillin-binding proteins (PBPs) are involved in the final stages of bacterial cell wall assembly. Two activities for PBPs are the cross-linking of the cell wall, carried out by DD-transpeptidases, and the DD-peptidase activity, that removes the terminal D-Ala residue from peptidoglycan. The DD-peptidase activity moderates the extent of the cell wall cross-linking. There exists a balance between the two activities that is critical for the well-being of bacterial cells. We have cloned and purified PBP5 of Escherichia coli. The membrane anchor of this protein was removed, and the enzyme was obtained as a soluble protein. Two fragments of the polymeric cell wall of Gram-negative bacteria (compounds 5 and 6) were synthesized. These molecules served as substrates for PBP5. The products of the reactions of PBP5 and compounds 5 and 6 were isolated and were shown to be D-Ala and the fragments of the substrates minus the terminal D-Ala. The kinetic parameters for these enzymic reactions were evaluated. PBP5 would appear to have the potential for turnover of as many as 1.4 million peptidoglycan strands within a single doubling time (i.e., generation) of E. coli.

  DOI：

  10.1021/jo035397e

文献信息

• Convenient Temporary Methyl Imidate Protection of <i>N</i>-Acetylglucosamine and Glycosylation at O-4
  作者：Anderson Cheng、Jenifer L. Hendel、Kimberley Colangelo、Michael Bonin、France-Isabelle Auzanneau

  DOI：10.1021/jo801117y

  日期：2008.10.3

  reactions, the 3-O-acylated methyl and ethyl imidates of glucosamine were shown to behave well during the glycosylation of the 4-OH with a variety of reaction conditions and various glycosyl donors. Glycosylation of these acceptors was successfully carried out with perbenzylated beta-thioethyl rhamnopyranoside under MeOTf promotion, while activation of this donor under NIS/TMSOTf or NIS/TfOH proved less

  当尝试在N-乙酰氨基葡萄糖受体的O-4处糖基化时，本文扩展了N-乙酰基暂时转化为烷基酰亚胺的范围和用途。描述了在位置4并在O-3处带有各种保护基的亚氨酸烷基酯保护的葡糖胺受体的优化合成。通过用0.5M MeOTf处理4-OH受体，立即在糖基化之前制备这些酰亚胺，以获得仍带有游离4-OH基团的相应的甲基酰亚胺。当在作为反应溶剂的乙醚中制备这些酰亚胺时，我们观察到除了所需的甲基酰亚胺外，还会出乎意料地形成乙基酰亚胺。尽管3-O-烯丙基受体非常不稳定，无法用于糖基化反应，在各种反应条件和各种糖基供体的作用下，在4-OH的糖基化过程中，葡糖胺的3-O-酰化的甲基和乙基酰亚胺被证明表现良好。这些受体的糖基化是在MeOTf促进下用过苄基的β-硫代乙基鼠李吡喃糖苷成功进行的，而在NIS / TMSOTf或NIS / TfOH下激活该供体则证明不太成功。相反，用NIS / TfOH活化反应性较低的全苄基化
• A method for the selective reduction of carbohydrate 4,6-O-benzylidene acetals
  作者：Michael P. DeNinno、John B. Etienne、Kimberly C. Duplantier

  DOI：10.1016/0040-4039(94)02348-f

  日期：1995.1

  Glucose-derived 4,6-O-benzylidene acetals can be selectively reduced to the corresponding 6-O-benzyl derivatives by the treatment with trifluoroacetic acid and triethylsilane.