benzyl 2-acetamido-2-deoxy-4-O-sulfonato-β-D-galactopyranoside sodium salt | 1276112-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-2-deoxy-4-O-sulfonato-β-D-galactopyranoside sodium salt
• 英文别名: benzyl-β-D-GalNAc(4SO4)；benzyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-d-galactopyranoside sodium salt；sodium;[(2R,3R,4R,5R,6R)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-3-yl] sulfate
• CAS: 1276112-92-5
• 化学式: C₁₅H₂₀NO₉S*Na
• 分子量: 413.381
• InChiKey: VGSYQLSGLOPJCR-SOHNQLJGSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.38
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  166
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-2-deoxy-4-O-sulfonato-β-D-galactopyranoside sodium salt 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 以95%的产率得到benzyl 2-acetamido-2-deoxy-4-O-sulfonato-β-D-galactopyranoside sodium
  参考文献：
  名称：

  Chondroitin-4-O-sulfatase from Bacteroides thetaiotaomicron: exploration of the substrate specificity

  摘要：

  Bacterial sulfatases can be good tools to increase the molecular diversity of glycosaminoglycan synthetic fragments. A chondroitin 4-O-sulfatase from the human commensal bacterium Bacteroides thetaiotaomicron has recently been identified and expressed. In order to use this enzyme for synthetic purposes, the minimal structure required for its activity has been determined. For that, four 4-O-sulfated monosaccharides and one 4-O-sulfated disaccharide have been synthesized and used as substrates with the sulfatase. The minimum structure was shown to be a disaccharide but in contrast to the natural substrate, which must have a 4,5-insaturation, the enzyme accepts as substrate, a disaccharide with a saturated glucuronic acid at the non-reducing end and even a glucopyranosyl moiety without the carboxylic acid functionality. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.03.033
• 作为产物：
  描述：

  在 甲醇 、 sodium methylate 作用下， 反应 16.0h， 生成 benzyl 2-acetamido-2-deoxy-4-O-sulfonato-β-D-galactopyranoside sodium salt
  参考文献：
  名称：

  Chondroitin-4-O-sulfatase from Bacteroides thetaiotaomicron: exploration of the substrate specificity

  摘要：

  Bacterial sulfatases can be good tools to increase the molecular diversity of glycosaminoglycan synthetic fragments. A chondroitin 4-O-sulfatase from the human commensal bacterium Bacteroides thetaiotaomicron has recently been identified and expressed. In order to use this enzyme for synthetic purposes, the minimal structure required for its activity has been determined. For that, four 4-O-sulfated monosaccharides and one 4-O-sulfated disaccharide have been synthesized and used as substrates with the sulfatase. The minimum structure was shown to be a disaccharide but in contrast to the natural substrate, which must have a 4,5-insaturation, the enzyme accepts as substrate, a disaccharide with a saturated glucuronic acid at the non-reducing end and even a glucopyranosyl moiety without the carboxylic acid functionality. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.03.033