2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-D-glucopyranose | 27537-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-D-glucopyranose
• 英文别名: GalNAc(β1->4)Gal(β1->4)Glc；GalNAc(b1-4)Gal(b1-4)Glc；N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 27537-68-4
• 化学式: C₂₀H₃₅NO₁₆
• 分子量: 545.495
• InChiKey: XGWWPIOYXPTSBV-UGMYLYQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  278
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-D-glucopyranose 、 3,6,9,12,15,18,21-heptaoxatricosanedihydrazide 反应 48.0h， 以58%的产率得到
  参考文献：
  名称：

  Bishydrazide Glycoconjugates for Lectin Recognition and Capture of Bacterial Pathogens

  摘要：

  Bishydrazides are versatile linkers for attaching glycans to substrates for lectin binding and pathogen detection schemes. The alpha,omega-bishydrazides of carboxymethylated hexa(ethylene glycol) (4) can be conjugated at one end to unprotected oligosaccharides, then attached onto carrier proteins, tethered onto activated carboxyl-terminated surfaces, or functionalized with a photoactive cross-linking agent for lithographic patterning. Glycoconjugates of bishydrazide 4 can also be converted into dithiocarbamates (DTCs) by treatment with CS2 under mild conditions, for attachment onto gold substrates. The immobilized glycans serve as recognition elements for cell-surface lectins and enable the detection and capture of bacterial pathogens such as Pseudomonas aeruginosa by their adsorption onto micropatterned substrates. A detection limit of 10(3) cfu/mL is demonstrated, using a recently introduced method based on optical pattern recognition.

  DOI：

  10.1021/bc100288c
• 作为产物：
  描述：

  2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-benzyl-D-glucopyranose 在 sodium methylate 、 20 % Pd(OH)2/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 13.0h， 以90%的产率得到2-acetamido-2-deoxy-β-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-D-glucopyranose
  参考文献：
  名称：

  Bishydrazide Glycoconjugates for Lectin Recognition and Capture of Bacterial Pathogens

  摘要：

  Bishydrazides are versatile linkers for attaching glycans to substrates for lectin binding and pathogen detection schemes. The alpha,omega-bishydrazides of carboxymethylated hexa(ethylene glycol) (4) can be conjugated at one end to unprotected oligosaccharides, then attached onto carrier proteins, tethered onto activated carboxyl-terminated surfaces, or functionalized with a photoactive cross-linking agent for lithographic patterning. Glycoconjugates of bishydrazide 4 can also be converted into dithiocarbamates (DTCs) by treatment with CS2 under mild conditions, for attachment onto gold substrates. The immobilized glycans serve as recognition elements for cell-surface lectins and enable the detection and capture of bacterial pathogens such as Pseudomonas aeruginosa by their adsorption onto micropatterned substrates. A detection limit of 10(3) cfu/mL is demonstrated, using a recently introduced method based on optical pattern recognition.

  DOI：

  10.1021/bc100288c

文献信息

• Bishydrazide Glycoconjugates for Lectin Recognition and Capture of Bacterial Pathogens
  作者：Avijit Kumar Adak、Alexei P. Leonov、Ning Ding、Jyothi Thundimadathil、Sumith Kularatne、Philip S. Low、Alexander Wei

  DOI：10.1021/bc100288c

  日期：2010.11.17

  Bishydrazides are versatile linkers for attaching glycans to substrates for lectin binding and pathogen detection schemes. The alpha,omega-bishydrazides of carboxymethylated hexa(ethylene glycol) (4) can be conjugated at one end to unprotected oligosaccharides, then attached onto carrier proteins, tethered onto activated carboxyl-terminated surfaces, or functionalized with a photoactive cross-linking agent for lithographic patterning. Glycoconjugates of bishydrazide 4 can also be converted into dithiocarbamates (DTCs) by treatment with CS2 under mild conditions, for attachment onto gold substrates. The immobilized glycans serve as recognition elements for cell-surface lectins and enable the detection and capture of bacterial pathogens such as Pseudomonas aeruginosa by their adsorption onto micropatterned substrates. A detection limit of 10(3) cfu/mL is demonstrated, using a recently introduced method based on optical pattern recognition.