辛基 2-乙酰氨基-2-脱氧-beta-D-吡喃半乳糖苷 | 383417-49-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 辛基 2-乙酰氨基-2-脱氧-beta-D-吡喃半乳糖苷
• 中文别名: 1-(4-氟苯基)-3-羰基-1H-异苯并呋喃-5-甲酰胺；辛基2-乙酰氨基-2-脱氧-beta-D-吡喃半乳糖苷；(2R)-2,3-二羟丙基-bD-吡喃半乳糖苷
• 英文名称: octyl-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: Octyl 2-Acetamido-2-deoxy-b-D-galactopyranoside；N-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-octoxyoxan-3-yl]acetamide
• CAS: 383417-49-0
• 化学式: C₁₆H₃₁NO₆
• 分子量: 333.425
• InChiKey: JXLKQDFJNOXCNT-IBEHDNSVSA-N

物化性质

• 熔点：
  200-202°C
• 溶解度：
  甲醇（微溶、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  辛醇 、 N′-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfonohydrazide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到辛基 2-乙酰氨基-2-脱氧-beta-D-吡喃半乳糖苷
  参考文献：
  名称：

  Protecting group-free immobilization of glycans for affinity chromatography using glycosylsulfonohydrazide donors

  摘要：

  A variety of applications in glycobiology exploit affinity chromatography through the immobilization of glycans to a solid support. Although several strategies are known, they may provide certain advantages or disadvantages in how the sugar is attached to the affinity matrix. Additionally, the products of some methods may be hard to characterize chemically due to non-specific reactions. The lack of specificity in standard immobilization reactions makes affinity chromatography with expensive oligosaccharides challenging. As a result, methods for specific and efficient immobilization of oligosaccharides remain of interest. Herein, we present a method for the immobilization of saccharides using N'-glycosylsulfonohydrazide (GSH) carbohydrate donors. We have compared GSH immobilization to known strategies, including the use of divinyl sulfone (DVS) and cyanuric chloride (CC), for the generation of affinity matrices. We compared immobilization methods by determining their immobilization efficiency, based on a comparison of the mass of immobilized carbohydrate and the concentration of active binding sites (determined using lectins). Our results indicate that immobilization using GSH donors can provide comparable amounts of carbohydrate epitopes on solid support while consuming almost half of the material required for DVS immobilization. The lectin binding capacity observed for these two methods suggests that GSH immobilization is more efficient. We propose that this method of oligosaccharide immobilization will be an important tool for glycobiologists working with precious glycan samples purified from biological sources. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.09.005

文献信息

• Protecting group-free immobilization of glycans for affinity chromatography using glycosylsulfonohydrazide donors
  作者：Daniel Hernandez Armada、Jobette T. Santos、Michele R. Richards、Christopher W. Cairo

  DOI：10.1016/j.carres.2015.09.005

  日期：2015.11

  A variety of applications in glycobiology exploit affinity chromatography through the immobilization of glycans to a solid support. Although several strategies are known, they may provide certain advantages or disadvantages in how the sugar is attached to the affinity matrix. Additionally, the products of some methods may be hard to characterize chemically due to non-specific reactions. The lack of specificity in standard immobilization reactions makes affinity chromatography with expensive oligosaccharides challenging. As a result, methods for specific and efficient immobilization of oligosaccharides remain of interest. Herein, we present a method for the immobilization of saccharides using N'-glycosylsulfonohydrazide (GSH) carbohydrate donors. We have compared GSH immobilization to known strategies, including the use of divinyl sulfone (DVS) and cyanuric chloride (CC), for the generation of affinity matrices. We compared immobilization methods by determining their immobilization efficiency, based on a comparison of the mass of immobilized carbohydrate and the concentration of active binding sites (determined using lectins). Our results indicate that immobilization using GSH donors can provide comparable amounts of carbohydrate epitopes on solid support while consuming almost half of the material required for DVS immobilization. The lectin binding capacity observed for these two methods suggests that GSH immobilization is more efficient. We propose that this method of oligosaccharide immobilization will be an important tool for glycobiologists working with precious glycan samples purified from biological sources. (C) 2015 Elsevier Ltd. All rights reserved.