(4,5-dimethoxy-2-nitrophenyl)methyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside | 302346-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4,5-dimethoxy-2-nitrophenyl)methyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
• 英文别名: (4,5-dimethoxy-2-nitrophenyl)methyl O-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-6-[(4,5-dimethoxy-2-nitrophenyl)methoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 302346-97-0
• 化学式: C₂₁H₃₁NO₁₅
• 分子量: 537.475
• InChiKey: DBFYNSMULMXKMN-GHEFTXHDSA-N

物化性质

• 沸点：
  814.6±65.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  243
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  glucose 1-phosphate 、 (4,5-dimethoxy-2-nitrophenyl)methyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 在 glucose-1-phosphate uridyltransferase 、 UDP葡萄糖-4-差向异构酶 creatine phosphate 、 α1,3-galactosyltransferase 、 creatine kinase 作用下， 反应 49.0h， 以63%的产率得到(4,5-dimethoxy-2-nitrophenyl)methyl α-D-galactopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Creatine Phosphate−Creatine Kinase in Enzymatic Synthesis of Glycoconjugates

  摘要：

  [GRAPHICS]Enzymatic production of glycoconjugates is hampered by expensive phosphagens such as acetyl phosphate (AcP) and phosphoenolpyruvate (PEP). Here, we introduce creatine phosphate-creatine kinase system as a novel and practical energy source in carbohydrate synthesis. This system was successfully demonstrated in the production of bioactive oligosaccharides with different sugar nucleotide regeneration systems.

  DOI：

  10.1021/ol034319a
• 作为产物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 (4,5-dimethoxy-2-nitrophenyl)methyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Characterization of an Anomeric Sulfur Analogue of CMP-Sialic Acid

  摘要：

  alpha-2,3-Sialyltransferase catalyzes the transfer of sialic acid from CMP-sialic acid (1) to a lactose acceptor. An analogue of 1 was synthesized in which the anomeric oxygen atom was replaced with a sulfur atom (1S). The key step in the synthesis of 1S was a tetrazole-promoted coupling of a cytidine-5'-phosphoramidite with a glycosyl thiol of a protected sialic acid. Compounds 1 and 1S were characterized for their activity in a sialyl transfer assay. The rate of solvolysis in aqueous buffer of analogue 1S was 50-fold slower than that of 1. Analogue 1S was found to be substrate for alpha-2,3-sialyltransferase. The K-m of 1S was just 3-fold higher than that of 1, while the k(cat) of 1S was 2 orders of magnitude lower compared to 1.

  DOI：

  10.1021/jo000646+

文献信息

• Synthesis and Characterization of an Anomeric Sulfur Analogue of CMP-Sialic Acid
  作者：Scott B. Cohen、Randall L. Halcomb

  DOI：10.1021/jo000646+

  日期：2000.9.1

  alpha-2,3-Sialyltransferase catalyzes the transfer of sialic acid from CMP-sialic acid (1) to a lactose acceptor. An analogue of 1 was synthesized in which the anomeric oxygen atom was replaced with a sulfur atom (1S). The key step in the synthesis of 1S was a tetrazole-promoted coupling of a cytidine-5'-phosphoramidite with a glycosyl thiol of a protected sialic acid. Compounds 1 and 1S were characterized for their activity in a sialyl transfer assay. The rate of solvolysis in aqueous buffer of analogue 1S was 50-fold slower than that of 1. Analogue 1S was found to be substrate for alpha-2,3-sialyltransferase. The K-m of 1S was just 3-fold higher than that of 1, while the k(cat) of 1S was 2 orders of magnitude lower compared to 1.
• Creatine Phosphate−Creatine Kinase in Enzymatic Synthesis of Glycoconjugates
  作者：Jianbo Zhang、Bingyuan Wu、Yingxin Zhang、Przemyslaw Kowal、Peng George Wang

  DOI：10.1021/ol034319a

  日期：2003.7.1

  [GRAPHICS]Enzymatic production of glycoconjugates is hampered by expensive phosphagens such as acetyl phosphate (AcP) and phosphoenolpyruvate (PEP). Here, we introduce creatine phosphate-creatine kinase system as a novel and practical energy source in carbohydrate synthesis. This system was successfully demonstrated in the production of bioactive oligosaccharides with different sugar nucleotide regeneration systems.