methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside | 678159-03-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5S,6R)-3-(3,4-dimethyl-2,5-dioxopyrrol-1-yl)-5-hydroxy-2-methoxy-6-(phenylmethoxymethyl)oxan-4-yl] acetate
• CAS: 678159-03-0
• 化学式: C₂₂H₂₇NO₈
• 分子量: 433.458
• InChiKey: CVYNHLBFLKBOLV-ACMVSEJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside 在 三氟甲磺酸 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Fragment of Bacterial Cell Wall

  摘要：

  Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.

  DOI：

  10.1021/jo035583k
• 作为产物：
  描述：

  1-((2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3,4-dimethyl-pyrrole-2,5-dione 在 吡啶 、 硼烷-三甲胺络合物 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 methyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-dimethylmaleimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Fragment of Bacterial Cell Wall

  摘要：

  Cell wall is indispensable for survival of bacteria. This large molecular "mesh" encases the entire cytoplasm of bacteria, and it is comprised of repeating backbone units of N-acetyl-glucosamine (NAG)-N-acetyl-muramic acid (NAM). A pentapeptide is attached to each of the lactyl units of the N-acetyl-muramic acid. The cell wall has both cross-linked and non-cross-linked components. In the present paper, we have devised a synthetic route for the preparation of a fragment of the cell wall comprised of a tetrasaccharide (NAG-NAM-NAG-NAM), along with the two appended peptides. We also report the syntheses of three glycosyl donors (compounds 5, 7, and 9) and three glycosyl acceptors (compounds 4, 6, and 8) based on the D-glucosamine structure as a building unit. The synthetic strategy that is disclosed is generally useful in construction of other natural products containing the D-glucosamine as a building block.

  DOI：

  10.1021/jo035583k

文献信息

• Deciphering the Nature of Enzymatic Modifications of Bacterial Cell Walls
  作者：Mijoon Lee、Dusan Hesek、Elena Lastochkin、David A. Dik、Bill Boggess、Shahriar Mobashery

  DOI：10.1002/cbic.201700293

  日期：2017.9.5

  Modifying cell walls: Homogeneous and heterogeneous octasaccharide peptidoglycans were synthesized for characterization of reactions of seven enzymes that modify the bacterial cell wall: SltB1, MltB, RlpA, mutanolysin, AmpDh2, AmpDh3, and PBP5. Three lytic transglycosylases and mutanolysin exhibited broadly distinct preferences for their substrate peptidoglycans in the reactions that they catalyze

  修饰细胞壁：合成均相和异相八糖肽聚糖，以表征修饰细菌细胞壁的7种酶的反应：SltB1，MltB，RlpA，变溶菌素，AmpDh2，AmpDh3和PBP5。三种裂解性转糖基化酶和变溶酶在其催化的反应中表现出对于其底物肽聚糖的广泛不同的偏好。