N-acryloyl-D-glucosamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acryloyl-D-glucosamine
• 英文别名: AGA；N-acryloylglucosamine；N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]prop-2-enamide
• 化学式: C₉H₁₅NO₆
• 分子量: 233.221
• InChiKey: AATRYIJEAAJBBP-JOHDSVJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丙烯酰胺 、 N-acryloyl-D-glucosamine 、 N-Acrylamido-D-glucosamine 、 N-(2-mercaptoethyl)-2,6-bis(4-benzoylbenzamido)hexanamide 、 偶氮二异丁腈 、 四甲基乙二胺 在 氮气 、 水 作用下， 以 dimethylsulfoxide(DMSO) 、 水 为溶剂， 反应 16.0h， 生成 2-deoxy-2-amino glucose
  参考文献：
  名称：

  Solid phase synthesis method and reagent

  摘要：

  一种试剂组成物，适用于涂覆在支撑表面上，以便为该表面提供高密度的反应基团。因此涂覆的表面可以用于任何适当的目的，特别适用于用作固相合成支持表面。反过来，合成支持表面可以用于重复和组合合成，例如核苷酸，多肽和多糖的合成。聚合涂层可用于提供增加的有效表面积，特别是在支持表面的有效面积本身受限的情况下，例如在硅晶片的表面上。这样，聚合涂层提供了反应密度和表面积或体积等性质的最佳组合。

  公开号：

  US06410643B1
• 作为产物：
  描述：

  2-(propiolamido)-2-deoxy-D-glucopyranose 在 [,14-bis(diphenylphosphino)butane] (1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 作用下， 以 氘代丙酮 、 氘代甲醇 为溶剂， 以60%的产率得到N-acryloyl-D-glucosamine
  参考文献：
  名称：

  Para-hydrogenated Glucose Derivatives as Potential ¹³C-Hyperpolarized Probes for Magnetic Resonance Imaging

  摘要：

  A set of molecules in which a glucose moiety is bound to a hydrogenable synthon has been synthesized and evaluated for hydrogenation reactions and for the corresponding para-hydrogen-induced polarization (PHIP) effects, in order to select suitable candidates for an in vivo magnetic resonance imaging (MRI) method for the assessment of glucose cellular uptake. It has been found that amidic derivatives do not yield any polarization enhancement, probably due to singlet-triplet state mixing along the reaction pathway. In contrast, ester derivatives are hydrogenated in high yield and afford enhanced H-1 and C-13 NMR spectra after para-hydrogenation. The obtained PHIP patterns are discussed and explained on the basis of the calculated spin level populations in the para-hydrogenated products. These molecules may find interesting applications in C-13 MRI as hyperpolarized probes for assessing the activity of glucose transporters in cells.

  DOI：

  10.1021/ja101399q

文献信息

• Investigating the Impact of Polymer Functional Groups on the Stability and Activity of Lysozyme–Polymer Conjugates
  作者：Melissa Lucius、Rebecca Falatach、Cameron McGlone、Katherine Makaroff、Alex Danielson、Cameron Williams、Jay C. Nix、Dominik Konkolewicz、Richard C. Page、Jason A. Berberich

  DOI：10.1021/acs.biomac.5b01743

  日期：2016.3.14

  Polymers are often conjugated to proteins to improve stability; however, the impact of polymer chain length and functional groups on protein structure and function is not well understood. Here we use RAFT polymerization to grow polymers of different lengths and functionality from a short acrylamide oligomer with a RAFT end group conjugated to lysozyme. We show by X-ray crystallography that enzyme structure is minimally impacted by modification with the RAFT end group. Significant activity toward the negatively charged Micrococcus lysodeicticus cell wall was maintained when lysozyme was modified with cationic polymers. Thermal and chemical stability of the conjugates was characterized using differential scanning fluorimetry and tryptophan fluorescence. All conjugates had a lower melting temperature; however, conjugates containing ionic or substrate mimicking polymers were more resistant to denaturation by guanidine hydrochloride. Our results demonstrate that tailoring polymer functionality can improve conjugate activity and minimize enzymatic inactivation by denaturants.

  聚合物常与蛋白质共轭以提高其稳定性；然而，聚合物链长和官能团对蛋白质结构和功能的影响尚未完全明了。本研究利用可逆加成断裂链转移（RAFT）聚合技术，从共轭于溶菌酶的带有RAFT端基的短丙烯酰胺寡聚体出发，合成了不同长度和官能化的聚合物。通过X射线晶体学分析表明，RAFT端基修饰对酶结构的影响微乎其微。溶菌酶经阳离子聚合物修饰后，对带负电的藤黄微球菌细胞壁仍保持显著活性。采用差示扫描荧光法和色氨酸荧光对共轭物的耐热性和化学稳定性进行了表征。所有共轭物的熔解温度均较低；然而，含有离子或模拟底物聚合物的共轭体对盐酸胍引起的变性具有更强的抵抗力。研究结果表明，通过调整聚合物官能团可以提高共轭物活性并减少酶因变性剂引起的失活。
• Novel glycopolymer hydrogels as mucosa-mimetic materials to reduce animal testing
  作者：Michael T. Cook、Sarah L. Smith、Vitaliy V. Khutoryanskiy

  DOI：10.1039/c5cc02428e

  日期：——

  Glycopolymer hydrogels capable of mimicking mucosal tissue in mucoadhesion testing have been designed.

  我们设计了能够在粘液粘附测试中模拟粘膜组织的聚糖水凝胶。
• JPH10298039A
  申请人：——

  公开号：JPH10298039A

  公开（公告）日：1998-11-10
• Para-hydrogenated Glucose Derivatives as Potential ¹³C-Hyperpolarized Probes for Magnetic Resonance Imaging
  作者：Francesca Reineri、Daniela Santelia、Alessandra Viale、Erika Cerutti、Luisa Poggi、Tomas Tichy、Samuel S. D. Premkumar、Roberto Gobetto、Silvio Aime

  DOI：10.1021/ja101399q

  日期：2010.5.26

  A set of molecules in which a glucose moiety is bound to a hydrogenable synthon has been synthesized and evaluated for hydrogenation reactions and for the corresponding para-hydrogen-induced polarization (PHIP) effects, in order to select suitable candidates for an in vivo magnetic resonance imaging (MRI) method for the assessment of glucose cellular uptake. It has been found that amidic derivatives do not yield any polarization enhancement, probably due to singlet-triplet state mixing along the reaction pathway. In contrast, ester derivatives are hydrogenated in high yield and afford enhanced H-1 and C-13 NMR spectra after para-hydrogenation. The obtained PHIP patterns are discussed and explained on the basis of the calculated spin level populations in the para-hydrogenated products. These molecules may find interesting applications in C-13 MRI as hyperpolarized probes for assessing the activity of glucose transporters in cells.
• Solid phase synthesis method and reagent
  申请人：SurModics, Inc.

  公开号：US06410643B1

  公开（公告）日：2002-06-25

  A reagent composition adapted to be coated onto a support surface in order to provide that surface with a high density of reactive groups. The surface, thus coated, can be used for any suitable purpose, and is particularly well suited for use as a solid phase synthesis support surface. The synthesis support surface, in turn, can be used in repetitive and combinatorial syntheses such as the synthesis of polynucleotides, polypeptides and polysaccharides. The polymeric coating can be used to provide increased effective surface area, particularly in situations in which the effective area of the support surface is itself limited, as on the surface of a silicon wafer. In so doing, the polymeric coating provides an optimal combination of such properties as reactive density and surface area or volume.

  一种试剂组成物，适用于涂覆在支撑表面上，以便为该表面提供高密度的反应基团。因此涂覆的表面可以用于任何适当的目的，特别适用于用作固相合成支持表面。反过来，合成支持表面可以用于重复和组合合成，例如核苷酸，多肽和多糖的合成。聚合涂层可用于提供增加的有效表面积，特别是在支持表面的有效面积本身受限的情况下，例如在硅晶片的表面上。这样，聚合涂层提供了反应密度和表面积或体积等性质的最佳组合。