3-[N-(5-oxohexanoyl)-L-phenylalanyl-L-glutamyl-O-benzyl-L-phenylalanyl-L-glycinyl]-aminopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 1256846-95-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-[N-(5-oxohexanoyl)-L-phenylalanyl-L-glutamyl-O-benzyl-L-phenylalanyl-L-glycinyl]-aminopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• CAS: 1256846-95-3
• 化学式: C₄₉H₆₄N₆O₁₄
• 分子量: 961.079
• InChiKey: FEVKNFQLDISQJN-PGONGAFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  69.0
• 可旋转键数：
  28.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  297.12
• 氢给体数：
  9.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3-[N-(5-oxohexanoyl)-L-phenylalanyl-L-glutamyl-O-benzyl-L-phenylalanyl-L-glycinyl]-aminopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以71%的产率得到3-[N-(5-oxohexanoyl)-L-phenylalanyl-L-glutamyl-L-phenylalanyl-L-glycinyl]-aminopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Artificial Golgi Apparatus: Globular Protein-like Dendrimer Facilitates Fully Automated Enzymatic Glycan Synthesis

  摘要：

  Despite the growing importance of synthetic glycans as tools for biological studies and drug discovery, a lack of common methods for the routine synthesis remains a major obstacle. We have developed a new method for automated glycan synthesis that employs the enzymatic approach and a dendrimer as an ideal support within the chemical process. Recovery tests using a hollow fiber ultrafiltration module have revealed that monodisperse G6 (MW = 58 kDa) and G7 (MW = 116 kDa) poly(amidoamine) dendrimers exhibit a similar profile to BSA (MW = 66 kDa). Characteristics of the globular protein-like G7 dendrimer with high solubility and low viscosity in water greatly enhanced throughput and efficiency in automated synthesis while random polyacrylamide-based supports entail significant loss during the repetitive reaction/separation step. The present protocol allowed for the fully automated enzymatic synthesis of sialyl Lewis X tetrasaccharide derivatives over a period of 4 days in 16% overall yield from a simple N-acetyl-D-glucosamine linked to an aminooxy-functionalized G7 dendrimer.

  DOI：

  10.1021/ja106955j
• 作为产物：
  描述：

  oxo-FE(OBn)FG-OH 、 3-aminopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以84%的产率得到3-[N-(5-oxohexanoyl)-L-phenylalanyl-L-glutamyl-O-benzyl-L-phenylalanyl-L-glycinyl]-aminopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Artificial Golgi Apparatus: Globular Protein-like Dendrimer Facilitates Fully Automated Enzymatic Glycan Synthesis

  摘要：

  Despite the growing importance of synthetic glycans as tools for biological studies and drug discovery, a lack of common methods for the routine synthesis remains a major obstacle. We have developed a new method for automated glycan synthesis that employs the enzymatic approach and a dendrimer as an ideal support within the chemical process. Recovery tests using a hollow fiber ultrafiltration module have revealed that monodisperse G6 (MW = 58 kDa) and G7 (MW = 116 kDa) poly(amidoamine) dendrimers exhibit a similar profile to BSA (MW = 66 kDa). Characteristics of the globular protein-like G7 dendrimer with high solubility and low viscosity in water greatly enhanced throughput and efficiency in automated synthesis while random polyacrylamide-based supports entail significant loss during the repetitive reaction/separation step. The present protocol allowed for the fully automated enzymatic synthesis of sialyl Lewis X tetrasaccharide derivatives over a period of 4 days in 16% overall yield from a simple N-acetyl-D-glucosamine linked to an aminooxy-functionalized G7 dendrimer.

  DOI：

  10.1021/ja106955j