N-methacryloylglucosamine | 17377-64-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methacryloylglucosamine
• 英文别名: 2-(methacrylamido)glucopyranose；N-methacryloyl D-glucosamine；2-methyl-N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]prop-2-enamide
• CAS: 17377-64-9
• 化学式: C₁₀H₁₇NO₆
• 分子量: 247.248
• InChiKey: LXDQROPOJYHQLE-OXNFMAJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  三甲基氯硅烷 、 N-methacryloylglucosamine 在 吡啶 、 六甲基二硅氮烷 作用下， 反应 0.03h， 生成 2-Deoxy-2-methacrylamido-tetra-O-(timethylsilyl)-D-glucopyranose
  参考文献：
  名称：

  Carbohydrate Protease Conjugates: Stabilized Proteases for Peptide Synthesis

  摘要：

  The synthesis of oligopeptides using stable carbohydrate protease conjugates (CPCs) was examined in acetonitrile solvent systems. CPC[alpha-chymotrypsin] was used for the preparation of peptides containing histidine, phenylalanine, tyrosine, and tryptophan in the P-1 position in 60-93% yield. The CPC[alpha-chymotrypsin]-catalyzed synthesis of octamer Z-Gly-Gly-Phe-Gly-Gly-Phe-Gly-Gly-OEt from Z-Gly-Gly-Phe-Gly-Gly-Phe-OMe was achieved in 71% yield demonstrating that synthesis was the dominant kinetic process relative to amide hydrolysis. CPC[papain] was used to synthesize peptides containing both hydrophilic and hydrophobic amino acids. The Pt specificity of papain for aromatic residues was utilized for the 2 + 3 coupling of Z-Tyr-Gly-OMe to H2N-Gly-Phe-Leu-OH to generate the leucine enkephalin derivative in 79% yield. Although papain is nonspecific for the hydrolysis of N-benzyloxycarbonyl amino acid methyl esters in aqueous solution, the rates of synthesis for these derivitives with nucleophile leucine tert-butyl ester differed by nearly 2 orders of magnitude. CPC[thermolysin] was used to prepare the aspartame precursor Z-Asp-Phe-OMe in 90% yield. The increased stability of CPCs prepared from periodate-modified poly(2-methacrylamido-2-deoxy-D-glucose), poly(2-methacrylamido-2-deoxy-D-galactcose) and poly(5-methacrylamido-5-deoxy-D-ribose), carbohydrate materials designed to increase the aldehyde concentration in aqueous solution, suggests that the stability of CPCs is directly related to the aldehyde concentration of the carbohydrate material. Periodate oxidation of poly(2-methacrylamido-2-deoxy-D-glucose) followed by covalent attachment to a-chymotrypsin gave a CPC with catalytic activity in potassium phosphate buffer at 90 degrees C for 2 h.

  DOI：

  10.1021/jo00112a049
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 、 甲基丙烯酰氯 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 N-methacryloylglucosamine
  参考文献：
  名称：

  糖聚合物和聚（β-氨基酯）基两亲性嵌段共聚物作为药物载体

  摘要：

  糖聚合物是具有侧链糖部分的合成大分子，广泛用于靶向癌细胞。它们通常被认为是两亲性嵌段共聚物的亲水片段，用于制造作为药物载体的胶束。一种新型两亲性嵌段共聚物，即聚(2-脱氧-2-甲基丙烯酰胺-d-葡萄糖-co -2-甲基丙烯酸羟乙酯) -b-聚(β-氨基酯)[P(MAG- co -HEMA) -b制备了具有活性癌细胞靶向潜力和pH响应性的[-PBAE]。分别通过可逆加成断裂链转移聚合和基于迈克尔加成的缩聚反应分别合成四嗪末端官能化P(MAG- co -HEMA)和降冰片烯末端官能化PBAE嵌段，然后进行端基转化。然后，通过简单混合，进行四嗪与降冰片烯基团之间的逆电子需求狄尔斯阿尔德反应，得到两亲性嵌段共聚物。在对嵌段共聚物的化学结构、pH 响应性和药物负载/释放进行表征后，获得了含有或不含阿霉素 (DOX)（一种模型抗癌药物）的 pH 响应性胶束。在 pH 6.75 左右，胶束在叔胺基团上表现出急剧的质子化/去质子化转变，并且

  DOI：

  10.1021/acs.biomac.2c01076

文献信息

• Affinity Polymers Tailored for the Protein A Binding Site of Immunoglobulin G Proteins
  作者：Patricia Latza、Patrick Gilles、Torsten Schaller、Thomas Schrader

  DOI：10.1002/chem.201402399

  日期：2014.9.1

  Rational design in combination with a screening process was used to develop affinity polymers for a specific binding site on the surface of immunoglobulin G (IgG) proteins. The concept starts with the identification of critical amino acid residues on the protein interface and their topological arrangement. Appropriate binding monomers were subsequently synthesized. Together with a sugar monomer (2–5 equiv)

  结合筛选过程的合理设计可用于开发针对免疫球蛋白G（IgG）蛋白表面上特定结合位点的亲和聚合物。该概念始于鉴定蛋白质界面上的关键氨基酸残基及其拓扑结构。随后合成适当的结合单体。将它们与水溶性的糖单体（2-5当量）和作为荧光标记的丹磺酰基单体（0.5当量）一起，在水溶液中进行各种组成的线性自由基共聚（例如，偶氮二异丁腈（AIBN），均质水） / DMF混合物）。经过超滤和冻干后，获得了无色干燥的水溶性粉末。NMR光谱和凝胶渗透色谱（GPC）表征表明分子量在30至500 kD之间，并确认了单体组成的保留以及不存在单体。在聚合物库（20-50个成员）的竞争性酶联免疫吸附测定（ELISA）屏幕中，很少有共聚物可以作为抗体Fc片段上A蛋白结合位点的强力和选择性结合剂。它们的单体组成精确地反映了在界面处发现的关键氨基酸。带电荷的和非极性结合单体的简单组合足以用于合成聚合物的选择性亚微摩尔IgG识别。通过
• Immunomodulating properties of homo-and copolymers of N-vinylamides
  作者：E. F. Panarin、N. P. Ivanova、A. T. Belokhvostova、L. S. Potapenkova

  DOI：10.1007/s11094-006-0078-7

  日期：2006.3

  A series of new water-soluble copolymers of methacrylamidoglucose (MAG) with N-vinylamides (N-vinylformamide and N-alkyl-N-vinylacetamides) have been synthesized and characterized as modulants in BALB/C mice (i.p. administration) and by the method of local gel hemolysis. The imunostimulant action was observed for poly(vinyl formamide) in a dose of 25, 10, and 5 mg/kg and for MAG copolymers with N-octyl-N-vinylacetamide in a dose of 50 and 10 mg/kg. The other copolymers did not exhibit significant activity.

  合成并表征了一系列新的甲基丙烯酰氨基葡萄糖（MAG）与N-乙烯基酰胺（N-乙烯基甲酰胺和N-烷基-N-乙烯基乙酰胺）的水溶性共聚物，作为BALB/C小鼠（腹腔给药）中的调节剂，并通过局部凝胶溶血法进行表征。在25、10和5 mg/kg剂量下观察到聚（乙烯基甲酰胺）的免疫刺激作用，在50和10 mg/kg剂量下观察到MAG与N-辛基-N-乙烯基乙酰胺的共聚物的免疫刺激作用。其他共聚物没有显示出明显的活性。
• Glycopolymer-coated iron oxide nanoparticles: shape-controlled synthesis and cellular uptake
  作者：Xiao Li、Meimei Bao、Yuyan Weng、Kai Yang、Weidong Zhang、Gaojian Chen

  DOI：10.1039/c4tb00852a

  日期：——

  Serum-stable glyco-nanoparticles with controlled shape were easily obtained and exhibit shape-dependent cell uptake behaviors as well as enhanced activity toward specific lectins.

  稳定的血清糖基纳米颗粒具有可控形状，易于获得，并表现出形状相关的细胞摄取行为，以及对特定凝集素的增强活性。
• Cosmetic compositions containing polymers produced in the presence of
  申请人：L'Oreal

  公开号：US04283384A1

  公开（公告）日：1981-08-11

  A cosmetic composition for application to the hair or skin comprises in an appropriate cosmetic vehicle at least one polymer produced by polymerizing an unsaturated monomer and a compound having at least one OH function, the said polymerization being carried out in an aqueous medium and in the presence of cerium ions.

  一种用于涂抹于头发或皮肤的化妆品组合物，包括至少一种聚合物，所述聚合物由聚合不饱和单体和至少具有一个OH功能的化合物制成，在适当的化妆品载体中，所述聚合反应在水介质中并在铈离子的存在下进行。
• COPOLYMERS INCLUDING CINCHONA ALKALOID COMPONENTS AND ONE OR MORE ACRYLAMIDE OR ACRYLATE CONTAINING COMPONENTS, COMPLEXES CONTAINING THE SAME, AND METHODS OF USING THE SAME
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US20190153212A1

  公开（公告）日：2019-05-23

  Copolymers polymerized from at least one or more cinchona alkaloid containing compounds; and an acrylamide containing monomer, an acrylate containing monomer, or combinations thereof. Complexes and methods utilizing such copolymers are also disclosed.

  本发明涉及由至少一个或多个含奎宁生物碱的化合物和一个含有丙烯酰胺的单体、一个含有丙烯酸酯的单体或其组合物聚合而成的共聚物。本发明还公开了利用这种共聚物的复合物和方法。