benzyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-galactopyranoside | 868744-51-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-galactopyranoside
• CAS: 868744-51-8
• 化学式: C₂₉H₂₉NO₈
• 分子量: 519.551
• InChiKey: MYVKGGKJMHXHHZ-MWRXUHODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  120.39
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-galactopyranoside 在 palladium dihydroxide 吡啶 、 palladium dihydroxide 、 sodium azide 、 氢气 、 sodium methylate 、 N,N-二异丙基乙胺 、 sodium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.17h， 生成 dibenzylphospho-2,4-acetamido-3-O-benzoyl-2,4,6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Investigating Bacterial N-Linked Glycosylation:  Synthesis and Glycosyl Acceptor Activity of the Undecaprenyl Pyrophosphate-Linked Bacillosamine

  摘要：

  The chemical synthesis and biological activity of undecaprenyl pyrophosphate bacillosamine (Und-PP-Bac), an obligatory intermediate in the asparagine-linked glycosylation pathway of Campylobacter jejuni, are reported. The key transformation involves the coupling of bacillosamine phosphate and undecaprenyl phosphate. The synthetic Und-PP-Bac can be used to investigate the activity of the enzyme PglA, which catalyzes the first glycosyl transfer in substrate biosynthesis for N-linked protein glycosylation in the pathogenic gram-negative bacterium. The availability of this synthetic substrate makes it possible to access polyprenyl-linked oligosaccharides, such as the GalNAc-alpha-1,3-bacillosamine-alpha-1-PP-Und intermediate, that will enable exploration of the remaining enzymes in the prokaryotic glycosylation pathway. Study of the bacterial glycosylation system will provide insight into the corresponding eukaryotic process, which is currently poorly understood.

  DOI：

  10.1021/ja054265v
• 作为产物：
  描述：

  D-半乳糖胺五乙酸酯 在 吡啶 、 sodium methylate 、 ytterbium(III) triflate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 benzyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  化学合成4-氟-N-乙酰基己糖胺尿苷二磷酸供体：糖胺聚糖合成中的链终止剂。

  摘要：

  使用化学方法和化学方法制备了非天然尿苷二磷酸（UDP）糖供体UDP-4-脱氧-4-氟-N-乙酰氨基葡萄糖（4FGlcNAc）和UDP-4-脱氧-4-氟-N-乙酰半乳糖胺（4FGalNAc）。化学酶合成依赖于N-乙酰氨基葡糖-1-磷酸尿嘧啶转移酶（GlmU）。然后将所得的非天然UDP-糖供体作为通过各种合酶催化的糖胺聚糖合成中的底物进行测试。UDP-4FGlcNAc被多杀巴斯德氏菌肝素合酶1转移到受体上，随后用作链终止剂。

  DOI：

  10.1021/acs.joc.6b02929

文献信息

• Synthesis of 4-Azido-<i>N</i>-acetylhexosamine Uridine Diphosphate Donors: Clickable Glycosaminoglycans
  作者：Xing Zhang、Dixy E. Green、Victor L. Schultz、Lei Lin、Xiaorui Han、Ruitong Wang、Alexander Yaksic、So Young Kim、Paul L. DeAngelis、Robert J. Linhardt

  DOI：10.1021/acs.joc.7b01787

  日期：2017.9.15

  Unnatural chemically modified nucleotide sugars UDP-4-N-3-GlcNAc and UDP-4-N-3-GalNAc were chemically synthesized for the first time. These unnatural UDP sugar products were then tested for incorporation into hyaluronan, heparosan, or chondroitin using polysaccharide synthases. UDP-4-N-3-GlcNAc served as a chain termination substrate for hyaluronan or heparosan synthases; the resulting 4-N-3-GlcNAc-terminated hyaluronan and heparosan were then successfully conjugated with Alexa Fluor 488 DIBO alkyne, demonstrating that this approach is generally applicable for labeling and detection of suitable glycosaminoglycans.