1,3,4,6-tetra-O-acetyl-2-acrylamido-2-deoxy-D-glucose | 847201-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-acrylamido-2-deoxy-D-glucose
• 英文别名: 2-deoxy-2-[(1-oxo-2-propen-1-yl)amino]-β-D-glucopyranose-1,3,4,6-tetraacetate；N-acryloyl 1,3,4,6-tetra-O-acetyl-β-D-glucosamine；[(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-(prop-2-enoylamino)oxan-2-yl]methyl acetate
• CAS: 847201-70-1
• 化学式: C₁₇H₂₃NO₁₀
• 分子量: 401.37
• InChiKey: KIJAHABOTFJYOT-LMHBHQSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-acrylamido-2-deoxy-D-glucose 在 1,4-dithio-D,L-threitol 、 磷酸 、 sodium methylate 、 magnesium chloride 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 P'-[2-(1-oxo-2-propen-1-yl)amino-2-deoxy-α-D-glucopyranosyl] ester uridine 5'-(trihydrogen diphosphate), disodium salt
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Uridine Diphosphate-GlcNAc and Uridine Diphosphate-GalNAc Analogs for the Preparation of Unnatural Glycosaminoglycans

  摘要：

  Eight N-acetylglucosamine-1-phosphate and N-acetylgalactosamine-1-phosphate analogs have been synthesized chemically and were tested for their recognition by the GlmU uridyltransferase enzyme. Among these, only substrates that have an amide linkage to the C-2 nitrogen were transferred by GlmU to afford their corresponding uridine diphosphate(UDP)-sugar nucleotides. Resin-immobilized GlmU showed comparable activity to nonimmobilized GlmU and provides a more facile final step in the synthesis of an unnatural UDP-donor. The synthesized unnatural UDP-donors were tested for their activity as substrates for glycosyltransferases in the preparation of unnatural glycosaminoglycans in vitro. A subset of these analogs was useful as donors, increasing the synthetic repertoire for these medically important polysaccharides.

  DOI：

  10.1021/jo202322k
• 作为产物：
  描述：

  2-(4-methoxybenzylidene)imine-2-deoxy-D-glucopyranose 在 吡啶 、 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 1,3,4,6-tetra-O-acetyl-2-acrylamido-2-deoxy-D-glucose
  参考文献：
  名称：

  [EN] NANOPARTICLES FOR DRUG-DELIVERY
  [FR] NANOPARTICULES POUR APPORT DE MEDICAMENT

  摘要：

  公开号：

  WO2005020933A3

文献信息

• Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light
  作者：Rajdip Chowdhury、Zhunzhun Yu、My Linh Tong、Stefanie V. Kohlhepp、Xiang Yin、Abraham Mendoza

  DOI：10.1021/jacs.0c09678

  日期：2020.11.25

  Photoexcited dihydronicotinamides like NADH and analogues have been found to generate alkyl radicals upon reductive decarboxylation of redox-active esters without auxiliary photocatalysts. This principle allowed aliphatic photocoupling between redox-active carboxylate derivatives and electron-poor olefins, displaying surprising water and air-tolerance and unusually high coupling rates in dilute conditions

  已经发现光激发的二氢烟酰胺（如 NADH 和类似物）在没有辅助光催化剂的情况下，在氧化还原活性酯的还原脱羧时产生烷基自由基。这一原理允许氧化还原活性羧酸盐衍生物和缺电子烯烃之间的脂肪族光耦合，显示出令人惊讶的防水和空气耐受性以及在稀释条件下异常高的耦合率。展示了在其他羧酸存在下反应的正交性及其在 DNA 功能化中的效用，特别是将可见光与 NADH（生命普遍存在的还原剂）结合使用。
• Design, synthesis, and evaluation of positron emission tomography/fluorescence dual imaging probes for targeting facilitated glucose transporter 1 (GLUT1)
  作者：Richard Yuen、Michael Wagner、Susan Richter、Jennifer Dufour、Melinda Wuest、Frederick G. West、Frank Wuest

  DOI：10.1039/d1ob00199j

  日期：——

  against 2-[18F]FDG in breast cancer cells. Radiolabeling with 18F was achieved through the synthesis of prosthetic group 7-fluoro-2,1,3-benzoxadiazole-4-sulfonyl [18F]fluoride ([18F]FBDF) followed by the reaction with glucosamine. The radiotracer was finally analyzed in vivo in a breast cancer xenograft model and compared to 2-[18F]FDG. Despite favourable in vitro fluorescence imaging properties, 2-[18F]FBDG

  增加能量代谢，然后增加葡萄糖消耗是癌症的标志。大多数癌细胞表现出促进型己糖转运蛋白 GLUT1 的过度表达，包括乳腺癌。GLUT1 是 2-deoxy-2-[ 18 F]fluoro - D - glucose ( 2-[ 18 F]FDG ) 的主要转运蛋白，是肿瘤学正电子发射断层扫描 (PET) 成像的金标准。本研究的目标是开发新的基于葡萄糖的双成像探针，用于串联 PET 和荧光 (Fl) 成像。用荧光团和18 F 标记标记的氨基葡萄糖支架应赋予 GLUT1 选择性。在五种不同的化合物中，2-deoxy-2-((7-sulfonylfluoro-2,1,3-benzoxadiazol-4-yl)amino) -D-葡萄糖 ( 2-FBDG ) 具有良好的荧光特性和与 2-deoxy-2-((7-nitro-2,1,3-benzoxadiazol-4-yl)amino)- D -glucose