2-chloro-4-nitrophenyl α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-4-nitrophenyl α-D-glucopyranoside
• 英文别名: 2-chloro-4-nitrophenyl-α-D-glucoside；2-Chloro-4-nitrophenyl-alpha-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-(2-chloro-4-nitrophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₂H₁₄ClNO₈
• 分子量: 335.698
• InChiKey: PJCVBKZRKNFZOD-ZIQFBCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 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：
  145
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-chloro-4-nitrophenyl α-D-glucopyranoside 生成 (2R,3R,4S,5S,6R)-2-(4-amino-2-chlorophenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  TOKUTAKEH, SEITI;YAMATSUGI, NOBUYUKI;TOMIKURA, MASASI;INABA, SIGEHYUKI

  摘要：

  DOI：
• 作为产物：
  描述：

  2-chloro-4-nitrophenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 氨 作用下， 以 甲醇 为溶剂， 以25%的产率得到2-chloro-4-nitrophenyl α-D-glucopyranoside
  参考文献：
  名称：

  区分水溶液中差向异构糖苷和α-和β-糖苷键的双核铜（II）配合物

  摘要：

  合成了两种手性双核铜（II）配合物，并首次将其表征为在接近中性pH的水溶液中水解芳基糖苷和二糖的有效化学选择性催化剂。在这些条件下，通过29倍不同的反应速率和3倍不同的催化剂熟练度观察到了差向异构体芳基α-吡喃葡萄糖苷。此外，α-和β的性质有很大的区别作为模型化合物的芳基糖苷中的β-糖苷键是显而易见的，但在选定的二糖中也注意到。详细讨论了配合物的手性和碳水化合物构型的作用对与催化剂相互作用的影响。最后，金属配合物催化水解的推定机理是从实验证据中得出的，该实验证据表明C-2处羟基的去质子化是糖苷水解的先决条件。

  DOI：

  10.1016/j.jcat.2015.12.026

文献信息

• GLYCOSYLTRANSFERASE REVERSIBILITY FOR SUGAR NUCLEOTIDE SYNTHESIS AND MICROSCALE SCANNING
  申请人：Thorson Jon S.

  公开号：US20130004979A1

  公开（公告）日：2013-01-03

  The present invention generally relates to materials and methods for exploiting glycosyltransferase reversibility for nucleotide diphosphate (NDP) sugar synthesis. The present invention provides engineered glycosyltransferase enzymes characterized by improved reaction reversibility and expanded sugar donor specificity as compared to corresponding non-mutated glycosyltransferase enzymes. Such reagents provide advantageous routes to NDP sugars for subsequent use in a variety of biomedical applications, including enzymatic and chemo-enzymatic glycorandomization.

  本发明一般涉及利用糖基转移酶可逆性合成核苷酸二磷酸（NDP）糖的材料和方法。本发明提供了改良反应可逆性并扩展糖供体特异性的工程糖基转移酶酶，与相应的非突变糖基转移酶酶相比，具有更好的反应可逆性和扩展的糖供体特异性。这些试剂提供了有利的NDP糖路线，用于随后在各种生物医学应用中使用，包括酶促和化学酶促糖随机化。
• An aromatic substituted glycoside
  申请人：HOECHST CELANESE CORPORATION

  公开号：EP0263435A2

  公开（公告）日：1988-04-13

  An aromatic substituted glycoside is disclosed of the formula wherein the configuration of the substituted -OR on the anomeric carbon is alpha, n is an integer of 0 or 1, and R is a substituted aromatic radical selected from the group where R through R6 are independently halogen, NO2, S03H, where R7 is lower alkyl; and includes its stereoisomers, optical isomers and geometric isomers and mixtures of the foregoing isomers. These substrates are useful as direct substrates for alpha-amylases. A process for the preparation of the substrates and related substances is also described.

  本发明公开了一种芳香族取代的糖苷，其式中，取代的-OR 在异构碳上的构型为α，n 为 0 或 1 的整数，R 为取代的芳香基，选自 R 至 R6 独立地为卤素、NO2、S03H 的基团，其中 R7 为低级烷基；并包括其立体异构体、光学异构体和几何异构体以及前述异构体的混合物。 这些底物可作为α-淀粉酶的直接底物。 本发明还描述了制备这些底物及相关物质的工艺。
• METHOD OF MEASUREMENT OF MATERIAL AND TESTPIECE
  申请人：KABUSHIKI KAISHA KYOTO DAIICHI KAGAKU

  公开号：EP0860695A1

  公开（公告）日：1998-08-26

  A method of measuring an analyte, comprising a step of measuring a detectable substance by using a reaction system including a formation reaction of the detectable substance based on a chemical reaction of the analyte contained in a sample, wherein a layered inorganic compound is caused to exist in the reaction system including the formation reaction of the detectable substance, whereby high-sensitivity measurement is made possible, the detectable substance can be stabilized to improve accuracy of the measurement, a rate of a chemical reaction is increased to enable quick measurement, and high-sensitivity measurement is made possible even in a reaction system which forms an insoluble substance. Also, it can be provided an analytical testing piece for measuring an analyte, by measuring a detectable substance by using a reaction system including a formation reaction of the detectable substance based on a chemical reaction of the analyte contained in a sample, wherein the testing piece comprises at least one test portion having a detection portion for detecting the detectable substance and contains a layered inorganic compound at least in the test portion, whereby diffusion and elution of a dyestuff or the like is prevented, more sensitive and accurate simple analysis is made possible, and easy handling is possible.

  一种测量被分析物的方法，包括以下步骤：根据样品中含有的被分析物的化学反应，使用包括可检测物质的形成反应的反应系统测量可检测物质，其中在包括可检测物质的形成反应的反应系统中导致层状无机化合物的存在、从而实现高灵敏度测量，稳定可检测物质以提高测量精度，提高化学反应速率以实现快速测量，即使在形成不溶性物质的反应体系中也能实现高灵敏度测量。此外，还可以提供一种用于测量被分析物的分析检测件，通过使用反应系统测量可检测物质，该反应系统包括基于样品中所含被分析物的化学反应的可检测物质的形成反应，其中检测件包括至少一个测试部分，该测试部分具有用于检测可检测物质的检测部分，并且至少在测试部分中包含分层无机化合物，从而防止染料或类似物的扩散和洗脱，实现更灵敏、更准确的简单分析，并且易于处理。
• Method for measuring substance and testing piece
  申请人：——

  公开号：US20030175984A1

  公开（公告）日：2003-09-18

  A method of measuring an analyte, comprising a step of measuring a detectable substance by using a reaction system including a formation reaction of the detectable substance based on a chemical reaction of the analyte contained in a sample, wherein a layered inorganic compound is caused to exist in the reaction system including the formation reaction of the detectable substance, whereby high-sensitivity measurement is made possible, the detectable substance can be stabilized to improve accuracy of the measurement, a rate of a chemical reaction is increased to enable quick measurement, and high-sensitivity measurement is made possible even in a reaction system which forms an insoluble substance. Also, it can be provided an analytical testing piece for measuring an analyte, by measuring a detectable substance by using, a reaction system including a formation reaction of the detectable substance based on a chemical reaction of the analyte contained in a sample, wherein the testing piece comprises at least one test portion having a detection portion for detecting the detectable substance and contains a layered inorganic compound at least in the test portion, whereby diffusion and elution of a dyestuff or the like is prevented, more sensitive and accurate simple analysis is made possible, and easy handling is possible.

  一种测量被分析物的方法，包括以下步骤：根据样品中含有的被分析物的化学反应，使用包括可检测物质的形成反应的反应系统测量可检测物质，其中在包括可检测物质的形成反应的反应系统中导致层状无机化合物的存在、从而实现高灵敏度测量，稳定可检测物质以提高测量精度，提高化学反应速率以实现快速测量，即使在形成不溶性物质的反应体系中也能实现高灵敏度测量。此外，还可以提供一种用于测量被分析物的分析检测件，通过使用反应系统测量可检测物质，该反应系统包括基于样品中所含被分析物的化学反应的可检测物质的形成反应，其中检测件包括至少一个测试部分，该测试部分具有用于检测可检测物质的检测部分，并且至少在测试部分中包含分层无机化合物，从而防止染料或类似物的扩散和洗脱，实现更灵敏、更准确的简单分析，并且易于处理。
• Study of the action of human salivary alpha-amylase on 2-chloro-4-nitrophenyl α-maltotrioside in the presence of potassium thiocyanate
  作者：Toshihiko Suganuma、Yoshiaki Maeda、Kanefumi Kitahara、Tomonori Nagahama

  DOI：10.1016/s0008-6215(97)00150-x

  日期：1997.9

  The degradation mechanism of a synthetic substrate, 2-chloro-4-nitrophenyl alpha-maltotrioside (CNP-G(3)), by human salivary alpha-amylase (HSA) was investigated by kinetic and product analyses. It was observed that the enzyme attacked the various CNP-maltooligosaccharides (CNP-G(3) to CNP-G(6)) releasing free CNP. Addition of 500 mM potassium thiocyanate (KSCN) was also found to greatly increase the rates of CNP-release. It was the fastest with CNP-G(3), and, in the presence of KSCN, was almost comparable to that of degradation of maltopentaose (G(5)). On the other hand, addition of KSCN decreased the rate of cleavage between glucan-glucan bonds in maltopentaose. Product analysis showed that KSCN addition altered the cleavage distribution which occurred 100% at the bond between CNP and G(3), and that product distribution of free CNP was largely dependent on substrate concentration. Formation of CNP-G,, a larger product than the original substrate CNP-G,, was found to be present in the digest at high concentrations of substrate and in the presence of KSCN. Based on these results, a degradation pathway for CNP-G(3) involving transglycosylation besides direct hydrolysis is proposed. The increase of the CNP-release by the addition of KSCN would result from a corresponding increase in the interaction between the CNP moiety and the corresponding subsite near the catalytic site, as well as the enhancement of the catalytic efficiency. (C) 1997 Elsevier Science Ltd.