methyl acetamido-2,6-anhydro-3,5-dideoxy-9-p-toluenesulfonyl-D-glycero-D-galactonon-2-enonate | 112824-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl acetamido-2,6-anhydro-3,5-dideoxy-9-p-toluenesulfonyl-D-glycero-D-galactonon-2-enonate
• 英文别名: methyl (2R,3R,4S)-3-acetamido-2-[(1R,2R)-1,2-dihydroxy-3-(4-methylphenyl)sulfonyloxypropyl]-4-hydroxy-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 112824-44-9
• 化学式: C₁₉H₂₅NO₁₀S
• 分子量: 459.474
• InChiKey: POEJUCRTSMAOJD-QBBQCFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl acetamido-2,6-anhydro-3,5-dideoxy-9-p-toluenesulfonyl-D-glycero-D-galactonon-2-enonate 在 sodium azide 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 sodium 5-acetamido-2,6-anhydro-9-azido-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enoate
  参考文献：
  名称：

  霍乱弧菌唾液酸酶和人胞质唾液酸酶NEU2 † ‡ 选择性抑制剂的合成

  摘要：

  唾液酸酶或神经氨酸酶催化唾液酸寡糖和糖缀合物中末端唾液酸残基的水解。尽管成功开发了专门针对流感病毒神经氨酸酶的有效抑制剂，但设计和合成针对细菌和人唾液酸酶的选择性抑制剂的进展仍很缓慢。在唾液酸酶底物特异性研究和唾液酸酶晶体结构分析的指导下，合成了许多在C9或在C5和C9处均被修饰的2-脱氧-2,3-脱氢-N-乙酰神经氨酸（DANA或Neu5Ac2en）类似物。各种细菌唾液酸酶和人类胞浆唾液酸酶NEU2的抑制研究表明，Neu5Gc9N 3 2en和Neu5AcN 3 9N 32en分别是针对霍乱弧菌唾液酸酶和人NEU2的选择性抑制剂。

  DOI：

  10.1039/c2ob25335f
• 作为产物：
  描述：

  methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 methyl acetamido-2,6-anhydro-3,5-dideoxy-9-p-toluenesulfonyl-D-glycero-D-galactonon-2-enonate
  参考文献：
  名称：

  霍乱弧菌唾液酸酶和人胞质唾液酸酶NEU2 † ‡ 选择性抑制剂的合成

  摘要：

  唾液酸酶或神经氨酸酶催化唾液酸寡糖和糖缀合物中末端唾液酸残基的水解。尽管成功开发了专门针对流感病毒神经氨酸酶的有效抑制剂，但设计和合成针对细菌和人唾液酸酶的选择性抑制剂的进展仍很缓慢。在唾液酸酶底物特异性研究和唾液酸酶晶体结构分析的指导下，合成了许多在C9或在C5和C9处均被修饰的2-脱氧-2,3-脱氢-N-乙酰神经氨酸（DANA或Neu5Ac2en）类似物。各种细菌唾液酸酶和人类胞浆唾液酸酶NEU2的抑制研究表明，Neu5Gc9N 3 2en和Neu5AcN 3 9N 32en分别是针对霍乱弧菌唾液酸酶和人NEU2的选择性抑制剂。

  DOI：

  10.1039/c2ob25335f

文献信息

• Photoaffinity Labeling of Sialidase with a Biotin-Conjugated Phenylaminodiazirine Derivative of 2,3-Didehydro-2-deoxy-N-acetylneuraminic Acid
  作者：Ramaswamy Kannappan、Masayuki Ando、Kimio Furuhata、Yutaka Uda

  DOI：10.1248/bpb.31.352

  日期：——

  A biotin-conjugated photoactivatable phenylaminodiazirine derivative of 2,3-didehydro-2-deoxy-N-acetylneuraminic acid (DANA) was synthesized to identify sialidase. The free carboxylic group and N-acetyl substituent of sialic acid, which are important for recognition and enzymatic activity of sialidase, were conserved by the photolabeling compound as confirmed using analytical methods. The synthesized compound and DANA competitively inhibited starfish sialidase with a Ki value of 7.6 μM and 4.6 μM, respectively. Photo incorporation of the labeling compound to sialidase increased with irradiation time; 90% photo incorporation was achieved with more than 10-min irradiation, and labeling was completely inhibited by the addition of a competitive inhibitor. Starfish sialidase purified using high-performance gel filtration chromatography was subjected to photoaffinity labeling. A 50-kDa band was revealed to contain the sialidase active site by the photolabeling compound, and labeling was completely hindered in presence of the competitive inhibitor. Labeling specificity was ensured by the addition of the heat-deactivated standard protein chymotrypsinogen A to the reaction mixture.

  合成了一种 2,3-二脱氢-2-脱氧-N-乙酰神经氨酸（DANA）的生物素共轭可光激活的苯氨基二氮氨酸衍生物，用于识别硅氨酸酶。光标记化合物保留了硅氨酸的游离羧基和 N-乙酰取代基，这两个基团对硅氨酸酶的识别和酶活性非常重要，这一点已通过分析方法得到证实。合成的化合物和 DANA 能竞争性地抑制海星的硅糖苷酶，其 Ki 值分别为 7.6 μM和 4.6 μM。标记化合物与硅糖苷酶的光结合随辐照时间的延长而增加；超过 10 分钟的辐照可使光结合率达到 90%，加入竞争性抑制剂可完全抑制标记。用高效凝胶过滤色谱法纯化的海星硅糖苷酶进行了光亲和标记。光标记化合物揭示出一条 50 kDA 的条带含有硅糖苷酶的活性位点，在竞争性抑制剂存在的情况下，标记完全受阻。在反应混合物中加入热失活的标准蛋白糜蛋白酶原 A 可确保标记的特异性。
• Synthesis of a Neu2en5Ac analog hapten and isolation of monoclonal antibody to Neu2en5Ac
  作者：Hiroya Kamei、Yasuhiro Kajihara、Yoshisuke Nishi

  DOI：10.1016/s0008-6215(99)00023-3

  日期：1999.2

  Neu2en5Ac is a minor component of body fluids and is abundant in sialuria, but no antibody to detect it has been reported. 5-Acetamido-2,6-anhydro-9-glutaramido-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid has been synthesized and conjugated with keyhole limpet hemocyanin (KLH) for immunization. A hybridoma named SIC172 was obtained that produces a monoclonal antibody (MAb) to Neu2en5Ac. SIC172 MAb in culture supernatant bound strongly to the hapten conjugated to BSA in ELISA, but slightly to fetuin, a glycoprotein which is rich in Neu5Ac. SIC172 MAb (IgG3(kappa)), purified with a protein A/G affinity column, bound strongly to fetuin. Neu2en5Ac competed with the MAb in binding in amounts as low as 3 mu M, while the competition of Neu5Ac appeared at amounts of more than 300 mu M. SIC172 MAb is a unique MAb specific to Neu2en5Ac and might be useful for detecting Neu2en5Ac, which occurs naturally and in sialuria. (C) 1999 Elsevier Science Ltd. All rights reserved.