6-氯-3-吲哚基-D-吡喃半乳糖苷 | 138182-21-5

• 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: 6-氯-3-吲哚基-D-吡喃半乳糖苷
• 中文别名: 6-氯-3-吲哚基-β-D-吡喃半乳糖苷
• 英文名称: 6-chloro-1H-indol-3-yl-beta-D-galactopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-((6-Chloro-1H-indol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4S,5R,6R)-2-[(6-chloro-1H-indol-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 138182-21-5
• 化学式: C₁₄H₁₆ClNO₆
• 分子量: 329.737
• InChiKey: OQWBAXBVBGNSPW-MBJXGIAVSA-N

物化性质

• 熔点：
  188-190℃
• 沸点：
  630.2±55.0 °C(Predicted)
• 密度：
  1.641±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  避免使用强氧化剂

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  115
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25,S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29389090

反应信息

• 作为反应物：
  描述：

  6-氯-3-吲哚基-D-吡喃半乳糖苷 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 potassium phosphate 、 氯化镍二甲氧基乙烷 、 sodium hydride 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 96.17h， 生成 N-benzyl-6-formyl-3-indolyl-β-D-galactopyranoside tetraacetate
  参考文献：
  名称：

  通过氯自由基的光催化生成，使芳基氯化物发生温和的氧化还原中性甲酰化反应

  摘要：

  我们报告了芳基氯化物的氧化还原中性甲酰化反应，该反应是通过镍和光氧化还原催化作用对1,3-二氧戊环进行选择性2官能化而进行的。这种可扩展的台式方法相对于传统的还原羰基化具有明显的优势，因为它不使用一氧化碳，加压气体或化学计量的还原剂。温和的条件为丰富而复杂的芳基氯原料提供了空前的应用范围。

  DOI：

  10.1002/anie.201702079

文献信息

• Novel alizarin-based chromogenic substrates, their uses and composition containing same
  申请人：——

  公开号：US20030082667A1

  公开（公告）日：2003-05-01

  The invention concerns a novel chromogenic substrate based on Alizarin. The invention also concerns the uses to which this substrate can be put, and a formulation containing such a substrate. It consists therefore of a substrate to detect the presence of an enzyme activity, with the following general formula: 1 in which: the two ketone groups of the central ring can be replaced by one group R 11 (in the upper position), and by OH (in the lower position). R 1 is a target part or H, and R 2 is a target part or H, with at least one out of R 1 and R 2 being a target part, R 3 is H, SO 3 H, Cl, Br, F, I, NO 2 , NH 2 , NR 9 R 10 , or an Acylamino Aminoaryl or Aminoacylamino group of the type NHCOX, with X being an Alkyl, Aryl or Aralkyl group or an a-amino acid residue such as Alanine, R4 is H, SO 3 H, Cl, Br, F, I, NO 2 , NH 2 , NR 9 R 10 , OH or an Acylamino Aminoaryl or Aminoacylamino group of the type NHCOX, with X being an Alkyl, Aryl or Aralkyl group or an &agr;-amino acid such as Alanine, according to a modification, R 3 and R 4 form bonds with one another to create a ring with at least five sides, and preferably six sides. R 5 , R 6 , R 7 and R 8 each consist of one of the following atoms or groups of atoms: H, a halogen (particularly Cl or Br), OH, SO 3 H, or an Alkyl or Alkoxy group, and R 9 a R 10 are independently a Methyl, Alkyl, Aryl, Aralkyl group, or one (either R 9 or R 10 ) is a ring structure (Piperidine, Pyrrolidine, Morpholine, etc.) with the other (either R 10 or R 9 ) being a Hydrogen atom. The invention is particularly applicable in the field of diagnosis.

  这项发明涉及一种基于茜素的新型显色底物。该发明还涉及可以应用此底物的用途，以及含有这种底物的配方。因此，它包括一种用于检测酶活性存在的底物，具有以下一般公式：其中：中心环的两个酮基团可以被一个R11基团（在上部位置）和一个OH基团（在下部位置）取代。R1是目标部分或H，R2是目标部分或H，其中至少有一个是目标部分，R3是H、SO3H、Cl、Br、F、I、NO2、NH2、NR9R10或NHCOX类型的Acylamino Aminoaryl或Aminoacylamino基团，其中X是Alkyl、Aryl或Aralkyl基团或α-氨基酸残基，如丙氨酸，R4是H、SO3H、Cl、Br、F、I、 、NH2、NR9R10、OH或NHCOX类型的Acylamino Aminoaryl或Aminoacylamino基团，其中X是Alkyl、Aryl或Aralkyl基团或α-氨基酸，如丙氨酸，根据一种修改，R3和R4相互形成键，创建至少五边形，最好是六边形的环。R5、R6、R7和R8分别由以下原子或原子团组成：H、卤素（特别是Cl或Br）、OH、SO3H或Alkyl或Alkoxy基团，而R9和R10独立地是甲基、Alkyl、Aryl、Aralkyl基团，或者其中之一（R9或R10）是环结构（哌啶、吡咯烷、吗啉等），而另一个（R10或R9）是氢原子。该发明在诊断领域特别适用。
• [EN] CHROMOGENIC SUBSTRATES FOR BETA-D-GLUCURONIDASE ACTIVITY AND USE THEREOF FOR MICROBIAL DETECTION<br/>[FR] SUBSTRATS CHROMOGENES POUR L'ACTIVITE DE LA BETA-D-GLUCURONIDASE, ET UTILISATION DE CEUX-CI A DES FINS DE DETECTION MICROBIENNE
  申请人：GLYCOSYNTH LTD

  公开号：WO2015067926A1

  公开（公告）日：2015-05-14

  Chromogenic substrates for β-D-glucuronidase activity comprising monoglucuronides of some 1,2-dihydroxyaromatic derivatives. When cleaved these form soluble coloured conjugates with multivalent metal ions such as iron ions. The substrates may be used in conjunction with chromogenic substrates for other enzymes in microbial detection and identification especially involving liquid media. Microbes can be grown in the presence of the substrates and the compounds providing the metal ion. The substrates are particularly useful for detecting β-D-glucuronidase-positive E. coli. Some of the substrates are new compounds, these having the formula II: wherein X2 is independently selected from the group consisting of H, CH3, C2-C6 alkyl, a metal cation and a non-metal cation; wherein Y2 is independently selected from the group consisting of H, a metal cation and a non-metal cation; wherein R21 is H; wherein R24 is H or NO2; and wherein R22 and R23 are H or one is OH and the other is H, or R22 and R23 together form the group VII: -CR25=CR26-CR27=CR28- VII; wherein R25 to R28 are independently selected from H, OH, C1-C8 alkyl, C1- C8 alkoxy, C1-C8 hydroxyalkyl, halogen, nitro, C2-C24 acyl, C2-C24 acyloxy, C7-C24 aralkyl, C6-C24 aryl, sulfonyl and amido, provided that any vicinal groups R25-R28 are not both OH. Synthetic methods for making the compounds are described.

  β-D-葡萄糖苷酶活性的显色底物包括一些1,2-二羟基芳香衍生物的单葡萄糖醛酸酯。当被裂解时，这些底物会与多价金属离子（如铁离子）形成可溶的有色结合物。这些底物可以与微生物检测和鉴定中的其他酶的显色底物一起使用，尤其涉及液体培养基。微生物可以在存在这些底物和提供金属离子的化合物的情况下生长。这些底物特别适用于检测β-D-葡萄糖苷酶阳性的大肠杆菌。其中一些底物是新化合物，其化学式为II：其中X2独立选择自H、CH3、C2-C6烷基、金属阳离子和非金属阳离子组成；Y2独立选择自H、金属阳离子和非金属阳离子组成；R21为H；R24为H或NO2；R22和R23为H或其中一个为OH，另一个为H，或者R22和R23一起形成组VII：-CR25=CR26-CR27=CR28- VII；R25至R28独立选择自H、OH、C1-C8烷基、C1-C8烷氧基、C1-C8羟基烷基、卤素、硝基、C2-C24酰基、C2-C24酰氧基、C7-C24芳基烷基、C6-C24芳基、磺酰基和酰胺，前提是任何相邻的基团R25-R28均不是两个都是OH。描述了制备这些化合物的合成方法。
• Novel chromogenic substrates based on Alizarin, their applications and formulations containing such substrates
  申请人：Armstrong Lyle

  公开号：US20060172364A1

  公开（公告）日：2006-08-03

  An alizarin-based chromogenic substrate, a composition containing the substrate, and its use to detect the presence of an enzymatic activity. The substrate is particularly applicable in the field of biological diagnosis.

  一种基于茜素的显色底物、含有该底物的组合物及其用于检测酶活性的用途。该底物特别适用于生物诊断领域。
• BIOSENSORS UTILIZING INK JET-PRINTED BIOMOLECULE COMPATIBLE SOL GEL INKS AND USES THEREOF
  申请人：Brennan John D.

  公开号：US20120135437A1

  公开（公告）日：2012-05-31

  Novel solid-phase biosensors that utilize ink jet printing of biocompatible sol-gel based inks to create sensor strips are reported herein. Biomolecules and other reagents useful in bioassays to detect, for example, pathogenic microorganisms or toxic substances, are immobilized on a substrate, which can be paper based, by layering these substances between two layers of biomolecule compatible sol gel. The sol gel precursor solutions and solutions of the assay reagents are printed from separate nozzles in a layered approach which avoids clogging of the nozzles by the pre-mature gelling of the sol gel precursor solution. In certain embodiments of the application, a capture agent is used to concentrate a compound to be detected in specific areas on the substrate to facilitate detection.

  本文报道了利用喷墨打印生物相容性溶胶凝胶基墨水制作传感器条的新型固相生物传感器。生物分子和其他有用于生物测定的试剂，例如用于检测病原微生物或有毒物质，被固定在基底上（可以是纸张），通过在两层生物分子相容性溶胶凝胶之间堆叠这些物质来实现。溶胶凝胶前体溶液和生物测定试剂的溶液从分离的喷嘴中以分层的方式打印，避免了溶胶凝胶前体溶液过早凝胶导致喷嘴堵塞的问题。在本申请的某些实施例中，使用捕获剂将待检化合物浓缩在基底的特定区域，以便于检测。
• NON-TOXIC SOLVENT FOR CHROMOGENIC SUBSTRATE SOLUTION AND USES THEREOF
  申请人：Pierce Biotechnology, Inc.

  公开号：US20130316330A1

  公开（公告）日：2013-11-28

  The present invention relates to a non-toxic dipolar solvent for chromogenic substrate for detecting presence of lacZ gene and/or gene activity, which comprises a stabilizing amount of a solubilizing agent. The present invention also relates to a method for inducing lac operon in screening assay, comprising the step of contacting an agar plate with at least one essential oil in a concentration sufficient to induce the lac operon. The present invention further relates to a method for detecting the presence of bacteria, comprising the step of contacting an agar plate with at least one essential oil in a concentration sufficient to induce detection of the bacteria.

  本发明涉及一种用于检测lacZ基因和/或基因活性的非毒性偶极溶剂的染色底物，其中包括一定量的稳定剂。本发明还涉及一种诱导lac operon的筛选检测方法，包括将至少一种必需油以足够诱导lac operon的浓度接触于琼脂平板的步骤。本发明还涉及一种检测细菌存在的方法，包括将至少一种必需油以足够诱导细菌检测的浓度接触于琼脂平板的步骤。