4-硝基苯基-β-D-硫代半乳糖苷 | 1230-27-9

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-硝基苯基-β-D-硫代半乳糖苷
• 中文别名: 4-硝基苯基-Β-D-硫代半乳糖苷；4-硝基苯基-Beta-D-硫代半乳糖苷
• 英文名称: 4-nitrophenyl 1-thio-β-D-galactopyranoside
• 英文别名: p-nitrophenyl 1-thio-β-D-galactopyranoside；p-nitrothiophenyl β-D-galactopyranoside；p-nitrophenyl S-β-D-galactopyranoside；p-nitrophenyl β-D-thiogalactosidase；pNP 1-thio-β-D-galactopyranoside；4-Nitrophenyl 1-thio-beta-D-galactopyranoside；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(4-nitrophenyl)sulfanyloxane-3,4,5-triol
• CAS: 1230-27-9
• 化学式: C₁₂H₁₅NO₇S
• mdl: MFCD00038072
• 分子量: 317.32
• InChiKey: IXFOBQXJWRLXMD-IIRVCBMXSA-N

物化性质

• 熔点：
  167℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• WGK Germany：
  3
• 海关编码：
  29329990
• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  4-硝基苯基-β-D-硫代半乳糖苷 在 Aspergillus oryzae β-thiogalactosidase 作用下， 反应 0.17h， 生成 4-硝基苯硫醇
  参考文献：
  名称：

  Galactosylation of Thiol Group by β-Galactosidase

  摘要：

  在 D-半乳糖和 2-巯基乙醇的缩合反应中，β-半乳糖苷酶不仅催化了羟基，还催化了硫醇基的 β-半乳糖基化。根据快速原子轰击质谱法、红外光谱法和核磁共振谱法，确认了硫代半乳糖苷化产物为 2-羟乙基 S-β-D-半乳糖苷。在几种β-半乳糖苷酶中，黑曲霉β-半乳糖苷酶水解对硝基苯基 S-β-D-半乳糖苷的速度最快，生成硫代半乳糖苷产物的效率最高。Penicillim 多色酶与 A. oryzae 酶一样有效。然而，大肠杆菌、脆弱酵母菌、乳酸克鲁维酵母菌和环状芽孢杆菌的酶主要对羟基进行半乳糖基化，生成 O-半乳糖苷。在 2-巯基乙醇浓度约为 1.25 M 时，合成硫代半乳糖苷的效果最好；半乳糖浓度为 0.8-2.8 M 时，对硫代半乳糖苷的合成产量影响不大。

  DOI：

  10.1271/bbb.64.735
• 作为产物：
  描述：

  C₁₉H₂₃NO₁₀S 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以74%的产率得到4-硝基苯基-β-D-硫代半乳糖苷
  参考文献：
  名称：

  基于聚羟基烷基糠酸酯部分的霍乱毒素的S-半乳糖苷和非碳水化合物配体的合成，生物学评估，WAC和NMR研究

  摘要：

  报道了基于聚羟烷基糠酸酯部分的几种霍乱毒素的非碳水化合物配体的合成。其中一些已通过稳定且耐受良好的S与D-半乳糖相连糖苷键。它们代表了一种新型的不可水解的二齿配体，其特征在于半乳糖和聚羟烷基糠酸酯为药效基团残基，从而模仿了GM1神经节苷脂。通过弱亲和色谱法（WAC）测量了新化合物对霍乱毒素的亲和力。还通过饱和转移差异NMR实验研究了最佳候选物与该毒素的相互作用，该实验可以鉴定与蛋白质相互作用的配体的结合表位。有趣的是，基于聚羟烷基糠酸酯结构的非碳水化合物模拟物显示出最高的亲和力。

  DOI：

  10.1002/chem.201302786

文献信息

• A bovine glucuronidase for assembly of β-d-glucuronyl-(1–3)-6-O-sulfo-β-d-gluco- and galacto-pyranosyl linkages
  作者：Hirotaka Uzawa、Takehiro Nagatsuka、Hideo Hiramatsu、Yoshihiro Nishida

  DOI：10.1039/b516921f

  日期：——

  Glucuronidase-catalyzed transglycosylation was examined by using 4-nitrophenyl β-D-glucuronide (D-GlcA-O-pNP) as the glycosyl donor; when pNP 6-O-sulfo-β-D-gluco- and D-galacto-pyranosides were used as the acceptors, a bovine enzyme was found to construct β-D-GlcA-(1–3)-linkages with the 6-O-sulfo-sugars in both a site- and β-selective way.

  通过使用 4-硝基苯δ-D-葡萄糖醛酸（D-GlcA-O-pNP）作为糖基供体，研究了葡萄糖醛酸酶催化的转糖基化作用；当使用 pNP 6-O-磺酰基-δ-D-吡喃葡萄糖苷和 D-半乳糖苷作为受体时，发现一种牛酶能以位点选择性和δ选择性的方式与 6-O-磺酰基糖构建δ-D-GlcA-(1â3)-连接。
• Liposome comprising a novel phosphate as membrane constituent, liposome preparations and cosmetic preparations comprising said phosphate
  申请人：KAO CORPORATION

  公开号：EP0370491A2

  公开（公告）日：1990-05-30

  A novel monophosphate and a novel diphosphate prepared by a phosphatidyl transfer reaction of a phospholipid and an alcohol in the presence of phospholipase D are disclosed. The phosphates can independently or together form small and stable liposomes which can include active components therein. Cosmetic compositions comprising these phosphates or liposomes penetrate well into the hair and the skin, and exhibit long-lasting excellent moisture-retaining, beauty, skin-activation effects.

  本研究公开了一种新型单磷酸盐和一种新型二磷酸盐，它们是在磷脂酶 D 的存在下，通过磷脂和醇的磷脂酰转移反应制备的。这些磷酸盐可单独或共同形成小而稳定的脂质体，其中可包含活性成分。包含这些磷酸盐或脂质体的化妆品组合物可以很好地渗透到头发和皮肤中，并表现出持久的出色保湿、美容和活肤效果。
• System for detecting microbial contamination
  申请人：Nederlandse Organisatie voor Toegepast- Natuurwetenschappelijk Onderzoek TNO

  公开号：EP2062978A1

  公开（公告）日：2009-05-27

  The present invention relates to a system for detecting microbial contamination of a liquid specimen comprising a device for concentrating micro-organisms from a liquid specimen, having (i) a hypobaric chamber, (ii) a filter housing comprising a liquid-permeable bed of an adsorbent material and adapted for being fluidly connected to said hypobaric chamber, and (iii) a vacuum pump adapted for being fluidly connected to said hypobaric chamber, said system further comprising a kit for detection of micro-organisms adsorbed to said adsorbent material, wherein said kit is based on enzymatic detection using chromogenic and/or fluorescent substrate analogs.

  本发明涉及一种用于检测液体标本微生物污染的系统，该系统包括一个用于从液体标本中浓缩微生物的装置，该装置具有(i)一个低压室；(ii)一个过滤器外壳，该过滤器外壳包括一个由吸附材料构成的液体渗透床，并适于与所述低压室流体连接；以及(iii)一个真空泵，适于与所述低压室流体连接、和 (iii) 真空泵，用于与所述低压室流体连接，所述系统还包括用于检测吸附在所述吸附材料上的微生物的试剂盒，其中所述试剂盒基于使用发色性和/或荧光底物类似物的酶检测。
• Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors
  作者：Suoding Cao、Serge J. Meunier、Fredrik O. Andersson、Marie Letellier、René Roy

  DOI：10.1016/s0957-4166(00)86308-9

  日期：1994.11

  Mild and stereoselective arylthio glycoside syntheses were accomplished by inversion of configuration of glycosyl halides under phase transfer catalyzed conditions. Under such conditions, aryl alpha-thiosialosides having electron donating and withdrawing substituents were evaluated as active and latent thioglycosyl donors. A sialyl-alpha-(2-->6)-galactoside was prepared in good yield using the above strategy.
• Scope and Applications of "Active and Latent" Thioglycosyl Donors. Part 4
  作者：Suoding Cao、Fernando Hernández-Matéo、René Roy

  DOI：10.1080/07328309808002341

  日期：1998.5.1

  The relative reactivity of various thioglycosyl donors having ethyl, phenyl, or parasubstituted phenyl groups with electron donating (N-Ac) or electron withdrawing (NO2) substituents were compared using 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose (3) as standard glycosyl acceptor. The reactivity order was found to decrease from ethyl > phenyl > p-acetamidophenyl > p-nitrophenyl. In the latter situation, when the thioglycosyl donor was also equipped with "disarming" ester protecting groups, they were found to be inert or inactive toward common thiophilic promoters. Alternatively, it was possible to selectively activate the "armed" perbenzylated p-nitrophenyl 1-thio-beta-D-galactopyranoside (21) in the presence of the corresponding "disarmed" perbenzoylated p-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-galactopyranoside (15) which served as the glycosyl acceptor. When both "armed" perbenzylated thioglycosides 7 and 25 were used as thioglycosyl donor and thioglycosyl acceptor, respectively, the milder thiophilic promotor methyl triflate was required for chemoselective activation. These results further demonstrate the potential of "armed and disarmed" "active and latent" thioglycosides in blockwise oligosaccharide syntheses.