2-Thiosialic acid methyl ester peracetate | 104556-69-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Thiosialic acid methyl ester peracetate
• 英文别名: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-S-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosonate；methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-acetylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 104556-69-6
• 化学式: C₂₂H₃₁NO₁₃S
• 分子量: 549.553
• InChiKey: ZQTVFTACJQPOSW-QDRUEPRISA-N

物化性质

• 沸点：
  632.6±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  212
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2-Thiosialic acid methyl ester peracetate 在 甲醇 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 3 A molecular sieve 、 sodium 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.67h， 生成 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3S,4S,5R,6S)-2-benzoyloxymethyl-3,5-dihydroxy-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Hydrolase and sialyltransferase activities of Trypanosoma cruzi trans -sialidase towards NeuAc-α-2,3-Gal-β- O -PNP

  摘要：

  NeuAc-alpha -2,3-Gal-beta -O-PNP has been synthesised and its ability to act as a substrate for the hydrolase and transferase activities of Trypanosoma cruzi trans-sialidase have been investigated. The turn-over of this compound shows marked differences from the behaviour of NeuAc-MU. In addition, distinct differences in the action of T. cruzi trans-sialidase and Clostridium perfringens neuraminidase on NeuAc-alpha -2,3-Gal-beta -O-PNP were apparent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00611-9
• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 Dowex 50W-X₈-200(H⁺) 作用下， 以 二氯甲烷 为溶剂， 反应 90.0h， 生成 2-Thiosialic acid methyl ester peracetate
  参考文献：
  名称：

  Hydrolase and sialyltransferase activities of Trypanosoma cruzi trans -sialidase towards NeuAc-α-2,3-Gal-β- O -PNP

  摘要：

  NeuAc-alpha -2,3-Gal-beta -O-PNP has been synthesised and its ability to act as a substrate for the hydrolase and transferase activities of Trypanosoma cruzi trans-sialidase have been investigated. The turn-over of this compound shows marked differences from the behaviour of NeuAc-MU. In addition, distinct differences in the action of T. cruzi trans-sialidase and Clostridium perfringens neuraminidase on NeuAc-alpha -2,3-Gal-beta -O-PNP were apparent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00611-9

文献信息

• Probing a sialyltransferase’s recognition domain to prepare α(2,8)-linked oligosialosides and analogs
  作者：Ping Zhang、Amir J. Zuccolo、Wenling Li、Ruixiang Blake Zheng、Chang-Chun Ling

  DOI：10.1039/b908933k

  日期：——

  We report the first observation that a monosialyl residue is the essential structural element recognized by the enzyme CST-II; this has resulted in an attractive route to synthesize a series of α(2,8)-linked oligosialic acids and their thioanalogs in one step.

  我们首次观察到，单唾液酸残基是酶CST-II识别的关键结构要素；这一发现为一步合成一系列α(2,8)-连接的寡唾液酸及其硫代类似物开辟了一条有吸引力的途径。
• Carbohydrate Chips for Studying High-Throughput Carbohydrate−Protein Interactions
  作者：Sungjin Park、Myung-ryul Lee、Soon-Jin Pyo、Injae Shin

  DOI：10.1021/ja0391661

  日期：2004.4.1

  diverse carbohydrate probes, solution-phase parallel and enzymatic glycosylations were performed. Three model disaccharides were in parallel synthesized in solution-phase and used as carbohydrate probes for the fabrication of carbohydrate chips. Three enzymatic glycosylations on glass slides were consecutively performed to generate carbohydrate microarrays that contained the complex oligosaccharide, sialyl

  碳水化合物-蛋白质相互作用在生物体中起着重要的生物学作用。在大多数情况下，生物物理和生物化学方法已被用于研究这些生物分子相互作用。对阐明碳水化合物和蛋白质之间识别事件的高通量方法的开发关注较少。在目前开发用于监测碳水化合物-蛋白质相互作用的新型高通量工具的努力中，我们通过将马来酰亚胺连接的碳水化合物固定在硫醇衍生的载玻片上来制备碳水化合物微阵列，并使用这些微阵列进行凝集素结合实验。结果表明，具有不同结构特征的碳水化合物以与从基于溶液的测定中获得的那些相关联的相对结合亲和力选择性地结合到相应的凝集素。此外，还通过用碳水化合物微阵列确定可溶性碳水化合物的 IC(50) 值来定量分析凝集素对碳水化合物的结合亲和力。为了制造包含更多不同碳水化合物探针的碳水化合物芯片，进行了液相平行和酶促糖基化。在溶液相中平行合成了三种模型二糖，并将其用作制备碳水化合物芯片的碳水化合物探针。连续在载玻片上进行三个酶
• Compounds comprising sulfated nonulonic acid having antiviral activity
  申请人：Nissan Food Products Co., Ltd.

  公开号：US06337390B1

  公开（公告）日：2002-01-08

  In order to provide the anti-retrovirus active compound with low anti-coagulant action and low cytotoxicity, compounds comprising glycoside or the salt thereof wherein lipid is linked to position 2 of sialic acid having all hydroxyl groups at positions 4, 7, 8 and 9 completely sulfated, or KDN (2-keto-3-deoxy-D-glycero-2-nononic acid) having all hydroxyl groups at positions 4, 5, 7, 8 and 9 completely sulfated are provided.

  为了提供具有低抗凝作用和低细胞毒性的抗逆转录病毒活性化合物，提供了包含糖苷或其盐的化合物，其中脂质连接到唾液酸的第2位，其4、7、8和9位的所有羟基完全磺酸化，或者KDN（2-酮-3-脱氧-D-甘油酸）的4、5、7、8和9位的所有羟基完全磺酸化。
• Solid-phase synthesis of dendritic sialoside inhibitors of influenza A virus haemagglutinin
  作者：Ren� Roy、Diana Zanini、Serge J. Meunier、Anna Romanowska

  DOI：10.1039/c39930001869

  日期：——

  Efficient solid-phase synthesis of dendritic α-thiosialoside inhibitors of influenza A virus haemagglutinin are described using hyperbranched L-lysine core structures.

  报道了利用超支化L-赖氨酸核心结构实现树枝状α-硫代唾液酸抑制剂高效固相合成的方法，该抑制剂能够抑制甲型流感病毒血凝素。
• One pot synthesis of<i>thio</i>-glycosides<i>via</i>aziridine opening reactions
  作者：Nives Hribernik、Alice Tamburrini、Ermelinda Falletta、Anna Bernardi

  DOI：10.1039/d0ob01956a

  日期：——

  A one-pot aziridine opening reaction by glycosyl thiols generated in situ from the corresponding anomeric thio-acetates affords thio-glycosides with a pseudo-disaccharide structure and an N-linked tether. The scope of the one-pot aziridine opening reaction was explored on a series of mono- and disaccharides, creating a class of pseudo-glycosidic compounds with potential for further functionalization

  由相应的异头硫代乙酸酯原位产生的糖基硫醇进行的一锅氮丙啶开环反应提供了具有假二糖结构和N-连接系链的硫代糖苷。在一系列单糖和二糖上探索了单罐氮丙啶开环反应的范围，从而创建了一类具有进一步功能化潜力的假糖苷化合物。在反应条件下，糖基硫醇发生了意外的异构化反应，研究了温度，碱和溶剂对异构化反应的影响。对于甘露糖，鼠李糖和唾液酸衍生物，以良好至可接受的产率获得了单一异构体。硫磺类合成的糖模拟物可能会被各种凝集素识别，同时具有水解和酶促稳定性。可以将掺入糖模拟物中的氮官能团用于进一步的官能化，包括与连接子，支架或肽残基的束缚。