N'-(β-D-galactopyranosyl)-p-toluenesulfonohydrazide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N'-(β-D-galactopyranosyl)-p-toluenesulfonohydrazide
• 英文别名: N'-(β-galactopyranosyl)-p-toluenesulfonohydrazide；4-methyl-N'-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]benzenesulfonohydrazide
• 化学式: C₁₃H₂₀N₂O₇S
• 分子量: 348.377
• InChiKey: QFTMHKHHOVFAMI-KSSYENDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  癸醇 、 N'-(β-D-galactopyranosyl)-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， 反应 0.5h， 以71%的产率得到n-decyl-D-galactopyranoside
  参考文献：
  名称：

  Protecting-group-free O-glysosidation using p-toluenesulfonohydrazide and glycosyl chloride donors

  摘要：

  A range of N '-glycosylsulfonohydrazides (GSHs) display good reactivity but poor stereoselectivity in protecting- group-free O-glycosidations when a moderate excess of the model acceptor n-decanol is employed. This stable, readily-accessed class of donor may be more tractable for the glycosylation of non-volatile acceptors than Fischer's glycosidation conditions. It is possible to generate unprotected glycosyl chlorides from GSHs in situ. In an effort to find conditions to improve glycosidation stereoselectivity, methanolysis of unprotected glucosyl chloride under halide-ion exchange conditions was examined. Relative to its tetra-O-benzyl analogue, this donor displays moderate, inverted stereoselectivity and a significantly faster reaction rate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.019
• 作为产物：
  描述：

  D-吡喃葡萄糖 、 对甲苯磺酰肼 在 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以99%的产率得到N'-(β-D-galactopyranosyl)-p-toluenesulfonohydrazide
  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 Synthesis of Glycosyl 1–Phosphates
  作者：Landon John G. Edgar、Somnath Dasgupta、Mark Nitz

  DOI：10.1021/ol3019083

  日期：2012.8.17

  Glycosyl 1-phosphates enriched in the alpha-anomer are obtained without the use of protecting groups in two steps starting from the free hemiacetal. Condensation of free hemiacetals with toluenesulfonylhydrazide yields a range of glycosylsulfonohydrazide donors which can be oxidized using cupric chloride in the presence of phosphoric acid and the coordinating additive 2-methyl-2-oxazoline to give useful yields of the fully deprotected glycosyl 1-phosphates.
• 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.
• Protecting-group-free O-glysosidation using p-toluenesulfonohydrazide and glycosyl chloride donors
  作者：Rohan J. Williams、Caroline E. Paul、Mark Nitz

  DOI：10.1016/j.carres.2013.08.019

  日期：2014.3

  A range of N '-glycosylsulfonohydrazides (GSHs) display good reactivity but poor stereoselectivity in protecting- group-free O-glycosidations when a moderate excess of the model acceptor n-decanol is employed. This stable, readily-accessed class of donor may be more tractable for the glycosylation of non-volatile acceptors than Fischer's glycosidation conditions. It is possible to generate unprotected glycosyl chlorides from GSHs in situ. In an effort to find conditions to improve glycosidation stereoselectivity, methanolysis of unprotected glucosyl chloride under halide-ion exchange conditions was examined. Relative to its tetra-O-benzyl analogue, this donor displays moderate, inverted stereoselectivity and a significantly faster reaction rate. (C) 2013 Elsevier Ltd. All rights reserved.